Cyanosilylation of Aldehydes and Ketones Catalyzed by Nanocrystalline Magnesium Oxide

REFERENCES

• (a) Geregory , R. J. H. Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications . Chem. Rev. 1999 , 99 , 3649 – 3682 ; (b) Brunel, J.-M.; Holmes, I. P. Chemically catalyzed asymmetric cyanohydrin syntheses. Angew. Chem. Int. Ed. 2004, 43, 2752–2778; (c) Effenberger, F. Synthesis and reactions of optically active cyanohydrins. Angew. Chem. Int. Ed. 1994, 33, 1555–1564; (d) North, M. Synthesis and applications of non-racemic cyanohydrins. Tetrahedron: Asymmetry 2003, 14, 147–176.
   PubMed Web of Science ®Google Scholar
• (a) North , M. Catalytic asymmetric cyanohydrin synthesis . Synlett 1993 , 807 – 820 ; (b) Furin, G. G.; Vyazankin, O. A.; Gostevsky, B. A., Vyazankin, N. S. Tetrahedron report number 234: Synthetic aspects of the use of organosilicon compounds under nucleophilic catalysis conditions. Tetrahedron 1988, 44, 2675–2749; (c) Rasmussen, J. K.; Hielmann, S. M.; Krepski, L. R. In Advances in Silicon Chemistry; G. L. Larson (Ed.); JAI Press: London, 1991; vol. 1, p. 65; (d) Matthews, B. R.; Gountzos, H.; Jackson, W. R.; Watson, K. G. Synthesis of threo-3-aryl-2,3-dihydroxypropanoic acid derivatives with high optical purity. Tetrahedron Lett. 1989, 30, 5157–5158; (e) Ziegler, T.; Horsch, B.; Effenberger, F. A convenient route to (R)-α-hydroxy carboxylic acids and (2R)-1-amino-2-alkanols from (R)-cyanohydrins. Synthesis 1990, 575–578; (f) Jackson, W. R.; Jacobs, H. A.; Matthews, B. R.; Jayatilake, G. S.; Watson, K. G. Stereoselective syntheses of ephedrine and related 2-aminoalcohols of high optical purity from protected cyanohydrins. Tetrahedron Lett. 1990, 31, 1447–1450; (g) Effenberger, F.; Stelzer, U. Synthesis and stereoselective reactions of (R)-α-sulfonyl oxynitriles. Angew. Chem. Int. Ed. 1991, 31, 873–874.
   Web of Science ®Google Scholar
• (a) Kusumoto , T. ; Hanamoto , T. ; Hiyama, Takehera , S. ; Shoji , T. ; Osawa , T. ; Kuriyama , T. ; Nakamura , K. ; Fujisawa , T. Optically active O-acyl cyanohydrins as chiral dopants for ferro electric liquid crystals . Chem. Lett. 1990 , 1615 – 1618 ; (b) Kruse, C. G. In Chirality in Industry; A. N. Collins, G. Sheldrake, and J. Crosby (Eds.); Wiley: Chichester, 1992; chapter 14.
   Web of Science ®Google Scholar
• (a) Groutas , W. C. ; Felker , D. Synthetic applications of cyanotrimethylsilane, lodotrimethylsilane, azidotrimethylsilane, and methylthiotrimethylsilane . Synthesis 1980 , 861 – 868 , and references cited therein; (b) Fujji, A.; Sakaguchi, S.; Ishii, Y. An efficient synthesis of dinitrile derivatives by the reaction of oxime esters or acid anhydrides with cyanotrimethylsilane catalyzed by La(O i Pr)3. J. Org. Chem. 2000, 65, 6209–6212; (c) Kawasaki, Y.; Fujii, A.; Nakano, Y.; Sakaguchi, S.; Ishii, Y. Acetylcyanation of aldehydes with acetone cyanohydrin and isopropenyl acetate by Cp*2 Sm(thf)2. J. Org. Chem. 1999, 64, 4214–4216.
   Web of Science ®Google Scholar
• (a) Saravanan , P. ; Anand , R. V. ; Singh , V. R. Cu(OTf)2 catalyzed trimethylsilyl cyanide addition to carbonyl compounds . Tetrahedron Lett. 1998 , 39 , 3823 – 3824 ; (b) Yang, Y.; Wang, D. The addition of trimethylsilyl cyanide to carbonyl compounds using Yb(OTf)3 as Lewis acid catalyst. Synlett 1997, 1379–1380; (c) Surya, K. D.; Richard, A. G. Vanadyl triflate as an efficient and recyclable catalyst for trimethylsilyl cyanide addition to carbonyl compounds. J. Mol. Catal. A: Chem. 2005, 232, 123–125; (d) Gassman, P. G.; Talley, J. J. Cyanohydrins—A general synthesis. Tetrahedron Lett. 1978, 19, 3773–3776; (e) Curini, M.; Epifanio, M. C.; Rosati, O.; Rossi, M. Potassium exchanged zirconium hydrogen phosphate as heterogenous catalyst in cyanosilylation of carbonyl compounds. Synlett 1999, 315–316. (f) Greenlee, W. J.; Hangauer, D. G. Addition of trimethylsilyl cyanide to α-substituted ketones: Catalyst efficiency. Tetrahedron Lett. 1983, 24, 4559–4560.
   Web of Science ®Google Scholar
• (a) Tian , S.-K. ; Deng , L. A highly enantioselective chiral Lewis base–catalyzed asymmetric cyanation of ketones . J. Am. Chem. Soc. 2001 , 123 , 6195 – 6196 ; (b) Tian, S.-K.; Hong, R.; Deng, L. Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base. J. Am. Chem. Soc. 2003, 125, 9900–9901; (c) Denmark, S. E.; Chung, W. Lewis base catalyzed addition of trimethylsilyl cyanide to aldehydes. J. Org. Chem. 2006, 71, 4002–4005; (d) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. A facile synthesis of cyanohydrin trimethylsilys ethers by the addition reaction of trimethylsilyl cyanide with aldehydes under basic conditions. Chem. Lett. 1991, 537–540.
   PubMed Web of Science ®Google Scholar
• (a) Fetterly , B. M. ; Verkade , J. G. P(RNCH2CH2)N: Efficient catalysts for the cyanosilylation of aldehydes and ketones . Tetrahedron Lett. 2005 , 46 , 8061 – 8066 ; (b) Wang, Z.; Fetterly, B. M.; Verkade, J. G. P(MeNMCH2CH2)3N: An effective catalyst for trimethylsilycyanation of aldehydes and ketones. J. Org. Met. Chem. 2002, 646, 161–166.
   Web of Science ®Google Scholar
• (a) Song , J. J. ; Gallou , F. ; Reeves , J. T. ; Tan , Z. ; Yee , N. K. ; Senanayake , C. H. Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds . J. Org. Chem. 2006 , 71 , 1273 – 1276 ; (b) Suzuki, Y.; Bakar, A.; Kazuyuki Muramastsu, M. D.; Sato, M. Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes. Tetrahedron 2006, 62, 4227–4231.
   PubMed Web of Science ®Google Scholar
• (a) Baleizao , C. ; Gigante , B. ; Garcia , H. ; Corma , A. Vanadyl salen complexes covalently anchored to an imidazolium ion as catalysts for the cyanosilylation of aldehydes in ionic liquids . Tetrahedron Lett. 2003 , 44 , 6813 – 6816 ; (b) Baleizao, C.; Gigante, B.; Garcia, H.; Corma, A. Ionic liquids as green solvents for the asymmetric synthesis of cyanohydrins catalysed by VO(salen) complexes. Green Chem. 2002, 4, 272–274; (c) Kim, S. S.; Lee, S. H.; Kwak, J. M. Enantioselective cyanosilylation of ketones catalyzed by Mn(salen)/Ph3PO. Tetrahedron: Asymmetry 2006, 17, 1165–1169; (d) Kim, S. S.; Song, D. H. Asymmetric cyanohydrin synthesis catalyzed by Al(salen)/triphenylphosphine oxide. Eur. J. Org. Chem. 2005, 1777–1780; (e) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex. Tetrahedron Lett. 1999, 40, 8147–8150.
   Web of Science ®Google Scholar
• (a) Jenner , G. Addition of trimethylsilyl cyanide to aromatic ketones promoted by organic solutions of lithium salts . Tetrahedron Lett. 1999 , 40 , 491 – 494 ; (b) Kurono, N.; Yamaguchi, M.; Suzuki, K.; Ohkuma, T. Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones. J. Org. Chem. 2005, 70, 6530–6532; (c) Amurrio, I.; Cordoba, R.; Csaky, A. G.; Plumet, J. Tetrabutylammonium cyanide catalyzed diasteroselective cyanosilylation of chiral α-hydroxyketones. Tetrahedron 2004, 60, 10521–10524; (d) Raj, I. V. P.; Suryavanshi, G.; Sudalai, A. Organocatalytic activation of TMSCN by basic ammonium salts for efficient cyanation of aldehydes and imines. Tetrahedron Lett. 2007, 48, 7211–7214; (e) Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt. J. Am. Chem. Soc. 2005, 127, 12224–12225; (f) Wang, X.; Tian, S.-K. Catalytic cyanosilylation of ketones with simple phosphonium salt. Tetrahedron Lett. 2007, 48, 6010–6013.
   Web of Science ®Google Scholar
• (a) Ryu , D. H. ; Corey , E. J. Highly enantioselective cyanosilylation of aldehydes catalyzed by a chiral oxazaborolidinium ion . J. Am. Chem. Soc. 2004 , 126 , 8106 – 8107 ; (b) Ryu, D. H.; Corey, E. J. Enantioselective cyanosilylation of ketones catalyzed by a chiral oxazaborolidinium ion. J. Am. Chem. Soc. 2005, 127, 5384–5387; (c) Fuerst, D. E.; Jacobsen, E. N. Thiourea-catalyzed enantioselective cyanosilylation of ketones. J. Am. Chem. Soc. 2005, 127, 8964–8965; (d) Zuend, S. J.; Jacobsen, E. N. Cooperative catalysis by tertiary amino-thioureas: Mechanism and basis for enantioselectivity of ketone cyanosilylation. J. Am. Chem. Soc. 2007, 129, 15872–15883; (e) Brunel, J.-M.; Legrand, O.; Buono, G. Enantioselective trimethylsilylcyanation of aromatic aldehydes catalyzed by titanium alkoxide–chiral o-hydroxyarylphosphine oxides complexes. Tetrahedron: Asymmetry 1999, 10, 1979–1984; (f) Kim, S. S.; Kwak, J. M.; Rajagopal, G. Asymmetric cyanosilylation of aldehydes by chiral Ti-TADDOL complex. Bull. Korean Chem. Soc. 2006, 27, 1638–1640.
   PubMed Web of Science ®Google Scholar
• (a) Kanai , M. ; Hamashima , Y. ; Shibasaki , M. Design of a new bifunctional asymmetric catalyst from carbohydrates: Application to catalytic asymmetric cyanosilylation of aldehydes and acetophenone . Tetrahedron Lett. 2000 , 41 , 2405 – 2409 ; (b) Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. Catalytic enantioselective conjugate addition of cyanide to α,β-unsaturated N-acylpyrroles. J. Am. Chem. Soc. 2005, 127, 514–515; (c) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid–Lewis base bifunctional catalyst. Tetrahedron 2001, 57, 805–814; (d) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. A new bifunctional asymmetric catalysis: An efficient catalytic asymmetric cyanosilylation of aldehydes. J. Am. Chem. Soc. 1999, 121, 2641–2642; (e) Hamashima, Y.; Kanai, M.; Shibasaki, M. Catalytic enantioselective cyanosilylation of ketones. J. Am. Chem. Soc. 2000, 122, 7412–7413.
   Web of Science ®Google Scholar
• (a) Shen , K. ; Liu , X. ; Li , Q. ; Feng , X. Highly enantioselective cyanosilylation of ketones catalyzed by a bifunctional Ti(IV) complex . Tetrahedron 2008 , 64 , 147 – 153 ; (b) Qin, B.; Liu, X.; Shi, J.; Zheng, K.; Zhao, H.; Feng, X. Enantioselective cyanosilylation of α,α-dialkoxy ketones catalyzed by proline-derived in-situ-prepared N-oxide as bifunctional organocatalyst. J. Org. Chem. 2007, 72, 2374–2378; (c) Xiong, Y.; Huang, X.; Gou, S.; Huang, J.; Wen, Y.; Feng, X. Enantioselective cyanosilylation of ketones catalyzed by a nitrogen-containing bifunctional catalyst. Adv. Synth. Catal. 2006, 348, 538–544; (d) Shen, Y.; Feng. X.; Li, Y.; Zhang, G.; Jiang, Y. A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid–Lewis base bifunctional catalyst. Tetrahedron 2003, 59, 5667–5675; (e) Chen, F.; Qin, B.; Feng, X.; Zhang, G.; Jiang, Y. Enantioselective cyanosilylation of ketones catalyzed by double-activation catalysts with N-oxides. Tetrahedron 2004, 60, 10449–10460; (f) Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Enantioselective cyanosilylation of ketones by a catalytic double-activation method employing chiral Lewis acid and achiral N-oxide catalysts. Org. Lett. 2003, 5, 949–952; (g) Chen, F.; Zhou, H.; Liu, X.; Qin, B.; Feng, X.; Zhang, G.; Jiang, Y. Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide. Chem. Eur. J. 2004, 10, 4790–4797; (h) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Asymmetric cyanosilylation of ketones catalyzed by bifunctional chiral N-oxide titanium complex catalysts. Eur. J. Org. Chem. 2004, 129–137.
   Web of Science ®Google Scholar
• (a) Kantam , M. L. ; Sreekanth , P. ; Santhi , P. L. Cyanosilylation of carbonyl compounds catalyzed by a diamino-functionalised mesoporous catalyst . Green Chem. 2000 , 2 , 47 – 48 ; (b) Shen, Z.-L.; Ji, S.-J.; Loh, T.-P. Ionic liquid [omim][PF6] as an efficient and recyclable reaction media for the cyanosilylation of aldehydes without Lewis acid or any special activation. Tetrahedron Lett. 2005, 46, 3137–3139; (c) Onaka, M.; Higuchi, K.; Suguta, K.; Izumi, Y. Efficient solid catalyst system for cyanosilylation of carbonyl compounds with cyano trimethylsilane. Chem. Lett. 1989, 1393–1396; (d) Higuchi, K.; Onaka, M.; Izumi, Y. Efficient and regioselective cyanosilylation of cyclohex-2-enone and other unsaturated ketones over solid acid and base catalysts. J. Chem. Soc., Chem. Commun. 1991, 1035–1036; (e) Karimi, B.; Mani, L. M. A highly efficient and recyclable silica-based scandium(III) interphase catalyst for cyanosilylation of carbonyl compounds. Org. Lett. 2004, 6, 4813–4815; (f) Baleizao, C.; Gigante, B.; Garcia, H.; Corma. A. Vanadyl salen complexes covalently anchored to single-wall carbon nanotubes as heterogeneous catalysts for the cyanosilylation of aldehydes. J. Catal. 2004, 221, 77–84.
   Web of Science ®Google Scholar
• (a) Lucas , E. ; Decker , S. ; Khaleel , A. ; Seitz , A. ; Fultz , S. ; Ponce , A. ; Li , W. ; Carnes , C. ; Klabunde , K. J. Nanocrystalline metal oxides as unique chemical reagents/sorbents . Chem. Eur. J. 2001 , 7 , 2505 – 2510 ; (b) Schlogl, R.; Abd Hamid, S. B. Nanocatalysis: Mature science revisited or something really new? Angew. Chem. Int. Ed. 2004, 43, 1628–1637; (c) Bell, A. T. The impact of nanoscience on heterogeneous catalysis. Science 2003, 299, 1688–1691; (d) Carnes, C. L.; Klabunde, K. J.; Synthesis, isolation, and chemical reactivity studies of nanocrystalline zinc oxide. Langmuir 2000, 16, 3764–3772; (e) Klabunde, K. J.; Mulukutla, R. S. Nanoscale Materials in Chemistry; Wiley Interscience: New York, 2001; chapter 7, p. 223.
   PubMed Web of Science ®Google Scholar
• (a) Choudary , B. M. ; Kantam , M. L. ; Ranganath , K. V. S. ; Mahendar , K. ; Sreedhar , B. Bifunctional nanocrystalline MgO for chiral epoxy ketones via Claisen–Schmidt condensation–asymmetric epoxidation reactions . J. Am. Chem. Soc. 2004 , 126 , 3396 – 3397 ; (b) Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. Nanocrystalline MgO for asymmetric Henry and Michael reactions. J. Am. Chem. Soc. 2005, 127, 13167; (c) Choudary, B. M.; Ranganath, K. V. S.; Yadav, J.; Kantam, M. L. Synthesis of flavanones using nanocrystalline MgO. Tetrahedron Lett. 2005, 46, 1369–1371; (d) Choudary, B. M.; Mahendar, K.; Ranganath, K. V. S. Wadsworth–Emmons reactions catalyzed by nanocrystalline MgO. J. Mol. Catal. A: Chem. 2005, 234, 25–27; (e) Choudary, B. M.; Mahendar, K.; Kantam, M. L.; Ranganath, K. V. S.; Athar, T. The one-pot Wittig reaction: A facile synthesis of α,β-unsaturated esters and nitriles by using nanocrystalline magnesium oxide. Adv. Synth. Catal. 2006, 348, 1977–1985; (f) Kantam, M. L.; Ranganath, K. V. S.; Mahendar, K.; Chakrapani, L.; Choudary, B. M. Asymmetric Michael addition of malonates to enones catalyzed by nanocrystalline MgO. Tetrahedron Lett. 2007, 48, 7646–7649; (g) Kantam, M. L.; Mahendar, K.; Sreedhar, B.; Choudary, B. M. Synthesis of α-amino nitriles through Strecker reaction of aldimines and ketoimines by using nanocrystalline magnesium oxide. Tetrahedron 2008, 64, 3351–3360.
   PubMed Web of Science ®Google Scholar
• Jiao , Z. ; Feng , X. ; Liu , B. ; Chen. , F. ; Zhang , G. ; Jiang , Y. Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N′-dioxides . Eur. J. Org. Chem. 2003 , 3818 – 3826 .
   Web of Science ®Google Scholar
• (a) Jeevanandam , P. ; Klabunde , K. J. A study on adsorption of surfactant molecules on magnesium oxide nanocrystals prepared by an aerogel route . Langmuir 2002 , 18 , 5309 – 5313 ; (b) Richards, R.; Li, W.; Decker, S.; Davidson, C.; Koper, O.; Zaikovski, V.; Volodin, A.; Rieker, T.; Klabunde, K. J. Consolidation of metal oxide nanocrystals: Reactive pellets with controllable pore structure that represent a new family of porous, inorganic materials. J. Am. Chem. Soc. 2000, 122, 4921–4925; (c) Utamapanya, S.; Klabunde, K. J.; Schlup, J. R. Nanoscale metal oxide particles/clusters as chemical reagents: Synthesis and properties of ultrahigh surface area magnesium hydroxide and magnesium oxide. Chem. Mater. 1991, 3, 175–181; (d) Klabunde, K. J.; Stark, J.; Koper, O.; Mohs, C.; Park, D. G.; Decker, S.; Jiang, Y.; Lagadic, I.; Zhang, D. Nanocrystals as stoichiometric reagents with unique surface chemistry. J. Phys. Chem. 1996, 100, 12142–12153; (e) Choudary, B. M.; Mulukutla, R. S.; Klabunde, K. J. Benzylation of aromatic compounds with different crystallites of MgO. J. Am. Chem. Soc. 2003, 125, 2020–2021.
   Web of Science ®Google Scholar