Chemoselective Reduction and Transesterification of α-Keto Propargylic Esters Mediated by NaBH₄ and CeCl₃ · 7H₂O

REFERENCES

• (a) Stang , P. J. ; Diederich , F. (Eds.). Modern Acetylene Chemistry ; VCH : Weinheim , Germany , 1995 ; (b) Shi Shun , A. L. K. ; Tykwinski , R. R. Synthesis of naturally occuring polyynes. Angew. Chem. Int. Ed. 2006, 45, 1034–1057 .
   Google Scholar
• Li , T. ; Tamaraz , M. M. ; Zaks , A. Preparation of chiral propargylic alcohol and ester intermediates of himbacine analogs. PCT Int. Appl. WO patent 2006076565 , 2006 .
   Google Scholar
• Trost , B. M. ; Weiss , A. H. Catalytic enantioselective synthesis of adociacetylene B . Org. Lett. 2006 , 8 , 4461 – 4464 .
   PubMedGoogle Scholar
• Meyer , A. ; Flammang , M. ; Wermuth , C. G. Synthesis of 3-unsubstituted 2-hydroxy-4-oxoalkanoates . Synthesis 1976 , 832 – 832 .
   Google Scholar
• (a) Guo , M. ; Li , D. ; Zhang , Z. Novel synthesis of 2-oxo-3-butynoates by copper-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride . J. Org. Chem. 2003 , 68 , 10172 – 10174 ; (b) Tanaka , K. ; Shoji , T. ; Hirano , M. Cationic rhodium (I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones . Eur. J. Org. Chem. 2007 , 2687 – 2699 .
   PubMedGoogle Scholar
• (a) Luche , J. L. Lanthanides in organic chemistry, 1: Selective 1,2-reductions of conjugated ketones . J. Am. Chem. Soc. 1978 , 100 , 2226 – 2227 ; (b) Luche , J. L. ; Rodriguez-Hahn , L. ; Crabbe , P. Reduction of natural enones in presence of cerium trichloride . J. Chem. Soc., Chem. Commun. 1978 , 601 – 602 ; (c) Gemal , A. L. ; Luche , J. L. Lanthanoids in organic synthesis, 6: The reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: Synthetic and mechanistic aspects . J. Am. Chem. Soc. 1981 , 103 , 5454 – 5459 .
   Web of Science ®Google Scholar
• (a) Bartoli , G. ; Marcantoni , E. ; Sambri , L. The CeCl3 · nH2O/NaI system in organic synthesis: An efficient water-tolerant Lewis acid promoter. Synlett 2003, 2101–2106; (b) Yadav , J. S. ; Reddy , B. V. S. ; Rao , C. V. ; Chand , P. K. ; Prasad , A. R. A facile and selective cleavage of prenyl esters catalyzed by CeCl3 · 7 H2O-NaI. Synlett 2002, 137–139; (c) Yadav , J. S. ; Reddy , B. V. S. ; Reddy , M. S. ; Sabitha , G. A facile cleavage of ketone N,N-dimethylhydrazones by CeCl3 · 7H2O-SiO2. . Synlett 2001, 1134–1136; (d) Deo , D. M. ; Marcantoni , E. ; Torregiani , E. A simple, efficient, and general method for the conversion of alcohols into alkyl iodides by a CeCl3 · 7H2O/NaI system in acetonitrile. J. Org. Chem. 2000, 65, 2830–2833.
   Google Scholar
• Marotta , E. ; Foresti , E. ; Marcelli , T. ; Peri , F. ; Righi , P. ; Scardovi , N. ; Rosini , G. CeCl3 · 7H2O-NaI-catalyzed hydrooxocyclization of unsaturated 3-hydroxy esters . Org. Lett. 2002 , 4 , 4451 – 4453 .
   PubMedGoogle Scholar
• (a) Boruah , A. ; Baruah , M. ; Prajapati , D. ; Sandhu , J. S. Cerium-catalyzed Michael addition of 1,3-dicarbonyl compounds under microwave irradiation . Synth. Commun. 1998 , 28 , 653 – 658 ; (b) Bartoli , G. ; Bartolacci , M. ; Giuliani , A. ; Marcantoni , E. ; Massaccesi , M. ; Torregiani , E. Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3 · 7H2O/NaI system supported on alumina in solvent-free conditions . J. Org. Chem. 2005 , 70 , 169 – 174 .
   Web of Science ®Google Scholar
• Torregiani , E. ; Seu , G. ; Minassic , A. ; Appendino , G. Cerium(III) chloride–promoted chemoselective esterification of phenolic alcohols . Tetrahedron Lett. 2005 , 46 , 2193 – 2196 .
   Web of Science ®Google Scholar
• Khodaei , M. M. ; Khosropout , A. R. ; Kookhazadeh , M. Enamination of β-dicarbonyl compounds catalyzed by CeCl3 · 7H2O at ambient conditions: ionic liquids and solvent-free media . Synlett 2004 , 11 , 1980 – 1984 .
   Web of Science ®Google Scholar
• Bartoli , G. ; Giuliani , A. ; Marcantoni , E. ; Massaccesi , M. ; Melchiorre , P. ; Lanari , S. ; Sambri , L. Allylation of aldehydes promoted by the cerium(III) chloride heptahydrate/sodium iodide system: The dependence of regio- and stereocontrol on the reaction conditions . Adv. Synth. Catal. 2005 , 347 , 1673 – 1680 .
   Web of Science ®Google Scholar
• Plietker , B. ; Niggemann , M. RuCl3/CeCl3/NaIO4: A new bimetallic oxidation system for the mild and efficient dihydroxylation of unreactive olefins . J. Org. Chem. 2005 , 70 , 2402 – 2405 .
   PubMedGoogle Scholar
• Li , W. D. Z. ; Peng , Y. An effective and highly stereoselective julia olefination of cyclopropyl carbinol mediated by CeCl3 · 7H2O/NaI . Org. Lett. 2005 , 7 , 3069 – 3072 .
   PubMedGoogle Scholar
• Li , Z. ; Wang , Z. Y. ; Zhu , W. ; Xing , Y. L. ; Zhao , Y. L. CeCl3 · 7H2O-KI catalysed environtmentally friendly synthesis of N,N-disubstituted ureas in water under microwave irradiation . Synth. Commun. 2005 , 35 , 2325 – 2331 .
   Web of Science ®Google Scholar
• (a) Bose , D. S. ; Kumar , R. K. An efficient, high-yielding protocol for the synthesis of functionalized quinolines via tandem addition/annulation reaction of o-aminoaryl ketones with α -methylene ketones . Tetrahedron Lett. 2006 , 47 , 813 – 816 ; (b) Jia , C. S. ; Dong , Y. W. ; Tu , S. J. ; Wang , G. W. Microwave-assisted solvent-free synthesis of substituted 2-quinolones . Tetrahedron 2007 , 63 , 892 – 897 ; (c) Yadav , J. S. ; Reddy , B. V. S. ; Sathaiah , K. ; Vishnumurthy , P. First example of functionalization of activated quinolines by indoles using CeCl3 · 7H2O . Synlett 2005 , 18 , 2811 – 2813 .
   Web of Science ®Google Scholar
• Meng , Q. ; Sun , Y. ; Ratovelomanana-Vidal , V. ; Genet , J. P. ; Zhang , Z. CeCl3 · 7H2O: An effective additive in Ru-catalyzed enantioselective hydrogenation of aromatic α-ketoesters . J. Org. Chem. 2008 , 73 , 3842 – 3847 .
   PubMedGoogle Scholar
• Saravanan , T. ; Chadha , A. Biocatalytic deracemization of alkyl-2-hydroxy-4-arylbut-3-ynoates using whole cells of Candida parapsilosis ATCC 7330 . Tetrahedron: Asymmetry 2010 , 21 , 2973 – 2980 .
   Google Scholar
• Chadha , A. ; Baskar , B. Biocatalytic deracemisation of α-hydroxy esters: High yield preparation of (S)-ethyl 2-hydroxy-4-phenylbutanoate from the racemate. Tetrahedron: Asymmetry 2002, 13, 1461–1464; (b) Baskar , B. ; Pandian , N. G. ; Priya , K. ; Chadha , A. Deracemisation of aryl substituted a-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism. Tetrahedron 2005, 61, 12296–12306; (c) Padhi , S. K. ; Chadha , A. Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR. Tetrahedron: Asymmetry 2005, 16, 2790–2798; (d) Thangavel , V. ; Chadha , A. Preparation of optically pure (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates by Candida parapsilosis ATCC 7330–mediated deracemization of the racemates. Tetrahedron 2007, 63, 4126–4133; (e) Titu , D. ; Chadha , A. Enantiomerically pure allylic alcohols: Preparation by Candida parapsilosis ATCC 7330–mediated deracemization. Tetrahedron: Asymmetry 2008, 19(14), 1698–1701.
   Google Scholar
• (a) Larock , R. C. In Comprehensive Organic Transformation ; Wiley-VCH : New York , 1999 ; (b) Smith , M. B. ; March , J. In Advanced Organic Chemistry, , 5th ed. ; Wiley : New York , 2001 ; (c) Dhimitruka , L. ; SantaLucia , J. Jr. Investigation of the Yamaguchi esterification mechanism: Synthesis of a Lux-S enzyme inhibitor using an improved esterificaion method. Org. Lett. 2006, 8, 47–50 .
   Google Scholar
• (a) Green , T. W. ; Wuts , P. G. M. In Protective Groups in Organic Synthesis, , 3rd ed. ; Wiley : New York , 1999 ; (b) Otera , J. Transesterification. Chem. Rev. 1993, 93, 1449–1470, and references cited therein; (c) Guieysse , D. ; Salagnad , C. ; Monsan , P. ; Remaud-Simeon , M. Lipase-catalyzed enantioselective transesterification toward ester of 2-bromo-tolylacetic acids. Tetrahedron: Asymmetry 2003, 14, 317–323; (d) Chavan , S. P. ; Shivasankar , K. ; Sivappa , R. ; Kale , R. Zinc-mediated transesterification of β-ketoesters and coumarin synthesis. Tetrahedron Lett. 2002, 43, 8583–8586 .
   Google Scholar
• Palaniappan , S. ; Chandra Shekhar , R. Transesterification of ketoesters with alcohols using polyaniline salts as catalysts . Polym. Adv. Technol. 2004 , 15 , 140 – 143 .
   Web of Science ®Google Scholar
• (a) Solhy , A. ; Clark , J. H. ; Tahir , R. ; Sebti , S. ; Larzek , M. Transesterification catalyzed by solid, reusable apatite-zinc chloride catalysts . Green Chem. 2006 , 8 , 871 – 874 ; (b) Ghesti , G. F. ; Macedo , J. L. ; Parente , V. C. I. ; Dias , J. A. ; Dias , S. C. L. Synthesis, characterization, and reactivity of Lewis acid/surfactant cerium trisdodecylsulfate catalyst for transesterification and esterification reactions . Appl. Catal. A: Gen. 2009 , 355 , 139 – 147 .
   Web of Science ®Google Scholar
• (a) Ramalinga , K. ; Vijayalakshmi , P. ; Kaimal , T. N. B. A mild and efficient method for esterification and transesterification catalyzed by iodine . Tetrahedron Lett. 2002 , 43 , 879 – 882 ; (b) Shapiro , G. ; Marzi , M. Facile and selective O-alkyl transesterification of primary carbamates with titanium(IV) alkoxides . J. Org. Chem. 1997 , 62 , 7096 – 7097 ; (c) Rethberg , C. E. ; Fisher , C. H. Preparation and properties of the n-alkyl acrylates . J. Am. Chem. Soc. 1944 , 66 , 1203 – 1207 ; (d) Holmquist , C. R. ; Roskamp , E. J. A selective method for diacetate catalysed the direct conversion of aldehyde into β-keto esters with ethyl diazoacetate catalyzed by tin(II) chloride . J. Org. Chem. 1989 , 54 , 3258 – 3260 ; (e) Ranu , B. C. ; Dutta , P. ; Sarkar , A. A simple and efficient procedure for transesterification catalyzed by indium triiodide . J. Org. Chem. 1998 , 63 , 6027 – 6028 ; (f) Ponde , D. E. ; Deshpande , V. H. ; Bulbule , V. J. ; Sudalai , A. ; Gajare , A. S. Selective catalytic transesterification, transthiolesterification, and protection of carbonyl compounds over natural kaolinitic clay . J. Org. Chem. 1998 , 63 , 1058 – 1063 ; (g) Madje , B. R. ; Patil , P. T. ; Shindalkar , S. S. ; Benjamin , S. B. ; Shingare , M. S. ; Dongare , M. K. Facile transesterification of β-ketoesters under solvent-free condition using borate zirconia solid acid catalyst . Catal. Commun. 2004 , 5 , 353 – 357 .
   Web of Science ®Google Scholar
• (a) Suarez-Castillo , O. R. ; Montiel-Ortega , L. A. ; Fragoso-Vazquez , M. J. ; Melendez-Rodriguez , M. ; Sanchez-Zavala , M. Transesterifications mediated by t-BuNH2 . Tetrahedron Lett. 2008, 49, 996–999, and references cited therein; (b) Meth-Cohn , O. A simple, powerful, and efficient method for transesterification. J. Chem. Soc., Chem. Commun. 1986, 695–697; (c) Billman , J. H. ; Smith , W. T. Jr. ; Rendall , J. L. Anticonvulsants, V: Esters of γ-diethylamino-α-phenylbutyric acid. J. Am. Chem. Soc. 1947, 69, 2058–2059; (d) Choudary , B. M. ; Kantam , M. L. ; Reddy , C. V. ; Aranganathan , S. ; Santhi , P. L. ; Figueras , F. Mg–Al–O–t-Bu hydrotalcite: A new and efficient heterogeneous catalyst for trans-esterification. J. Mol. Catal. A: Chem. 2000, 159, 411–416; (e) Balaji , B. S. ; Chanda , B. M. Simple and high-yielding syntheses of β-keto esters catalysed by zeolites. Tetrahedron 1998, 54, 13237–13252; (f) Ilankumaran , P. ; Verkade , J. G. P(RNCH2CH2)3N: Efficient catalysts for transesterifications, acylations, and deacylations. J. Org. Chem. 1999, 64, 3086–3089.
   Google Scholar
• (a) Fernholz , E. ; Schloeder , D. ; Liu , K. K. C. ; Bradshaw , C. W. ; Haung , H. ; Janda , K. ; Lerner , R. A. ; Wong , C. H. Specificity of antibody-catalysed transesterification using enol esters: A comparision with lipase reactions . J. Org. Chem. 1992 , 57 , 4756 – 4761 ; (b) Priya , K. ; Chadha , A. Synthesis of hydrocinnamic esters by Pseudomonas cepacia lipase . Enzyme Microb. Technol. 2003 , 32 , 485 – 490 ; (c) Vidya , P. ; Chadha , A. The role of different anions in ionic liquids on Pseudomonas cepacia lipase–catalyzed transesterification and hydrolysis . J. Mol. Catal. B: Enzymatic 2009 , 57 , 145 – 148 ; (d) Wirsching , P. ; Ashley , J. A. ; Benkovic , S. J. ; Janda , K. D. ; Lerner , R. A. An unexpectedly efficient catalytic anitbody operating by ping-pong and induced fit mechanism . Science 1991 , 252 , 680 – 685 .
   Google Scholar
• (a) Coskun , N. ; Er , M. New alkoxyzinc salts–mediated chemoselective transesterification reactions . Turk. J. Chem. 2005 , 29 , 455 – 461 ; (b) Yang , Y. H. ; Shi , M. Lewis acid–mediated reactions of cyclopropyl aryl ketones with α-ketoesters: Facile preparation of 5,6-dihydropyran-2-ones . J. Org. Chem. 2005 , 70 , 10082 ; (c) Yang , Y. H. ; Shi , M. A stereoselective synthetic route to 1,6-dioxaspiro[4.4]non-3-en-2-ones from cyclopropyl alkyl ketones and α-ketoesters . Org. Lett. 2006 , 8 , 1709 – 1712 .
   Google Scholar
• Padhi , S. K. ; Chadha , A. Sodium borohydride reduction and selective transesterification of β-keto ester in a one-pot reaction under mild conditions . Synlett 2003 , 639 .
   Google Scholar
• (a) Lefour , J. M. ; Loupy , A. The effect of cations on nucleophilic additions to carbonyl compounds: carbonyl complexation control versus ionic association control. Application to the regioselectivity of addition of α-enones . Tetrahedron 1978 , 34 , 2597 – 2605 ; (b) Ohwada , T. Orbital-controlled stereoselections in sterically unbiased cyclic system . Chem. Rev. 1999 , 99 , 1337 – 1375 .
   Google Scholar
• Cockerill , A. F. ; Davies , G. L. O. ; Harden , R. C. ; Rackham , D. M. Lanthanide shift reagents for nuclear magnetic resonance spectroscopy . Chem. Rev. 1973 , 73 , 553 – 588 .
   Web of Science ®Google Scholar