Catalytic, asymmetric Strecker reactions catalysed by titanium(IV) and vanadium(V)(salen) complexes

Vanadium(V)(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protecte...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 17; no. 9; pp. 1449 - 1456
Main Authors Blacker, John, Clutterbuck, Lisa A., Crampton, Michael R., Grosjean, Christophe, North, Michael
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 15.05.2006
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ALPHA-AMINO NITRILES
CYANOHYDRINS
FACILE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
POTASSIUM CYANIDE
IMINES
HYDROGEN-CYANIDE
ALDEHYDES
REISSERT-TYPE REACTION
TRIMETHYLSILYL CYANIDE
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Summary:Vanadium(V)(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protected with a benzyl group and in which the imine bond is not sterically encumbered. (c) 2006 Elsevier Ltd. All rights reserved.
ISSN:0957-4166
DOI:10.1016/j.tetasy.2006.05.015