Highly Efficient Cyanosilylation of Aldehydes and Ketones under Microwave, Solvent‐Free, and Lewis Acid–Free Conditions

References

• Gregory , R. J. H. 1999 . Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications . Chem. Rev. , 99 : 3649 – 3682 . For reviews, see
   PubMed Web of Science ®Google Scholar
• Effenberger , F. 1999 . Enzyme‐catalyzed preparation and synthetic applications of optically active cyanohydrins . Chimia , 53 : 3 – 10 .
   Google Scholar
• Achard , T. R. J. , Clutterbuck , L. A. and North , M. 2005 . Asymmetric catalysis of carbon–carbon bond‐forming reactions using metal(salen) complexes . Synlett , : 1828 – 1847 .
   Google Scholar
• North , M. 2004 . Introduction of the cyano group by addition to a carbonyl group . Science Synth. , 19 : 235 – 284 .
   Google Scholar
• North , M. 2003 . Synthesis and applications of non‐racemic cyanohydrins . Tetrahedron: Asymmetry , 14 : 147 – 176 .
   Google Scholar
• Shen , Z.‐L. , Ji , S.‐J. and Loh , T.‐P. 2005 . 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. , 46 : 3137 – 3139 .
   Web of Science ®Google Scholar
• Kurono , N. , Yamaguchi , M. , Suzuki , K. and Ohkuma , T. 2005 . Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones . J. Org. Chem. , 70 : 6530 – 6532 .
   PubMed Web of Science ®Google Scholar
• Firouzabadi , H. , Iranpoor , N. and Jafari , A. A. 2005 . Dodecatungestophosphoric acid (H3PW12O40) as a solid green Brønsted acid catalyzes high yielding and efficient trimethylcyanosilylation reactions of aldehydes and ketones by trimethylsilyl cyanide . J. Organometal. Chem. , 690 : 1556 – 1559 .
   Google Scholar
• Brunel , J.‐M. and Holmes , I. P. 2004 . Chemically catalyzed asymmetric cyanohydrin syntheses . Angew. Chem., Int. Ed. , 43 : 2752 – 2778 . and references cited therein
   Google Scholar
• Kim , S. S. and Kwak , J. M. 2005 . Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al(salen)/triphenylphosphine oxide . Tetrahedron , 62 : 49 – 53 . Recent examples, see
   Google Scholar
• Rodríguez , B. , Pastó , M. , Jimeno , C. and Pericàs , M. A. 2006 . Parallel synthesis of modular chiral Schiff base ligands and evaluation in the titanium(IV) catalyzed asymmetric trimethylsilylcyanation of aldehydes . Tetrahedron: Asymmetry , 17 : 151 – 160 .
   Google Scholar
• Ryu , D. H. and Corey , E. J. 2005 . Enantioselective cyanosilylation of ketones catalyzed by a chiral oxazaborolidinium ion . J. Am. Chem. Soc. , 127 : 5384 – 5387 .
   PubMed Web of Science ®Google Scholar
• Liu , X. , Qin , B. , Zhou , X. , He , B. and Feng , X. 2005 . Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt . J. Am. Chem. Soc. , 127 : 12224 – 12225 .
   Google Scholar
• Fuerst , D. E. and Jacobsen , E. N. 2005 . Thiourea‐catalyzed enantioselective cyanosilylation of ketones . J. Am. Chem. Soc. , 127 : 8964 – 8965 .
   PubMed Web of Science ®Google Scholar
• Tian , S.‐K. , Hong , R. and Deng , L. 2003 . Catalytic asymmetric cyanosilylation of ketones with chiral lewis base. J. Am. Chem. Soc. . 125 : 9900 – 9901 .
   Google Scholar
• Deng , H. , Isler , M. P. , Snapper , M. L. and Hoveyda , A. H. 2002 . Aluminum‐catalyzed asymmetric addition of TMSCN to aromatic and aliphatic ketones promoted by an easily accessible and recyclable peptide ligand . Angew. Chem., Int. Ed. , 41 : 1009 – 1012 .
   PubMed Web of Science ®Google Scholar
• Yabu , K. , Masumoto , S. , Yamasaki , S. , Hamashima , Y. , Kanai , M. , Du , W. , Curran , D. P. and Shibasaki , M. 2001 . Switching enantiofacial selectivities using one chiral source: Catalytic enantioselective synthesis of the key intermediate for (20S)‐camptothecin family by (S)‐selective cyanosilylation of ketones . J. Am. Chem. Soc. , 123 : 9908 – 9909 .
   PubMedGoogle Scholar
• Tian , S.‐K. and Deng , L. 2001 . A highly enantioselective chiral Lewis base–catalyzed asymmetric cyanation of ketones . J. Am. Chem. Soc. , 123 : 6195 – 6196 .
   PubMed Web of Science ®Google Scholar
• Hamashima , Y. , Kanai , M. and Shibasaki , M. 2001 . Catalytic enantioselective cyanosilylation of ketones: Improvement of enantioselectivity and catalyst turn‐over by ligand tuning . Tetrahedron Lett. , 42 : 691 – 694 .
   Web of Science ®Google Scholar
• Hamashima , Y. , Kanai , M. and Shibasaki , M. 2000 . Catalytic enantioselective cyanosilylation of ketones . J. Am. Chem. Soc. , 122 : 7412 – 7413 .
   Web of Science ®Google Scholar
• Belokon , Y. N. , Green , B. , Ikonnikov , N. S. , North , M. and Tararov , V. I. 1999 . The asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by a bimetallic, chiral (salen)titanium complex . Tetrahedron Lett. , 40 : 8147 – 8150 .
   Google Scholar
• Belokon , Y. N. , Caveda‐Cepas , S. , Green , B. , Ikonnikov , N. S. , Khrustalev , V. N. , Larichev , V. S. , Moscalenko , M. A. , North , M. , Orizu , C. , Tararov , V. I. , Tasinazzo , M. , Timofeeva , G. I. and Yashkina , L. V. 1999 . The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes . J. Am. Chem. Soc. , 121 : 3968 – 3973 .
   Web of Science ®Google Scholar
• Tanaka , K. and Toda , F. 2000 . Solvent‐free organic synthesis . Chem. Rev. , 100 : 1025 – 1074 .
   PubMed Web of Science ®Google Scholar
• Hayes , B. L. 2002 . Microwave Synthesis Matthews, NE : CEM Publishing . For review of microwave promoted reactions
   Google Scholar
• Matsumoto , K. , Hamana , H. and Iida , H. 2005 . Compendium of cycloaddition reactions under high pressure . Helv. Chim. Acta , 88 : 2033 – 2234 .
   Web of Science ®Google Scholar
• Jenner , G. 1999 . Addition of trimethylsilyl cyanide to aromatic ketones promoted by organic solutions of lithium salts . Tetrahedron Lett. , 20 : 491 – 494 . However, see (a) Kumamoto, K.; Iida, H.; Hamana, H.; Kotsuki, H.; Matsumoto, K. Are multicomponent Strecker reactions of diketones with diamines under high pressure amenable to heterocyclic synthesis? Heterocycles 2005, 66, 675–681
   Google Scholar
• Torii , S. , Inokuchi , T. , Takagishi , S. , Horike , H. , Kuroda , H. and Uneyama , K. 1987 . Electrogenerated acid‐catalyzed reactions of acetals, aldehydes, and ketones with organosilicon compounds, leading to aldol reactions, allylations, cyanations, and hydride additions . Bull. Chem. Soc. Jpn. , 60 : 2173 – 2188 .
   Web of Science ®Google Scholar
• Baeza , A. , Najera , C. , de Gracia Retamosa , M. and Sansano , J. M. 2005 . Solvent‐free synthesis of cyanohydrin derivatives catalysed by triethylamine . Synthesis , : 2787 – 2797 .
   Google Scholar
• Costa , D. J. , Boutin , N. E. and Riess , J. G. 1974 . Action of phenyltetrafluorophosphorane on α‐ or β‐hydroxy esters, ketones, nitriles, ethers, and nitro alcohols. Route to α‐ or β‐fluorinated functional derivatives . Tetrahedron , 30 : 3793 – 3797 .
   Google Scholar
• Ogibin , Y. N. , Velibekova , D. S. , Katsin , M. I. , Troyanskii , E. I. and Nikishin , G. I. 1981 . Silver(I)‐catalyzed oxidation of alkanone cyanohydrins by peroxydisulfate ions: Generation, reactions of 1‐cyanoalkoxyl radicals . Izv. Akad. Nauk Gruz. SSSR, Ser. Khim. , : 149 – 156 .
   Google Scholar
• Armarego , E. L. F. and Tucker , P. G. 1979 . Quinazoline, XXIV: The synthesis of 2,4‐diazatetracyclo[7.3.1.17,11.01,6]tetradecanes (adamantano[1,2‐d]pyrimidines) . Aust. J. Chem. , 32 : 1805 – 1817 .
   Google Scholar