A one-pot esterification of chiral O-trimethylsilyl-cyanohydrins with retention of stereochemistry

Enantiomerically enriched O-TMS cyanohydrins have been transformed directly into O-acyl-cyanohydrins using various anhydrides or acid chlorides in the presence of catalytic amounts of scandium(III) triflate. The reaction occurs with full retention of stereochemistry and allows the convenient measure...

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Bibliographic Details
Published in:Tetrahedron letters 2002-08, Vol.43 (33), p.5715-5717
Main Authors: Norsikian, Stephanie, Holmes, Ian, Lagasse, Franz, Kagan, Henri B
Format: Article
Language:English
Subjects:
ee measurement
esterification
O-acyl-cyanohydrins
O-trimethylsilyl-cyanohydrins
scandium triflate
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Summary:Enantiomerically enriched O-TMS cyanohydrins have been transformed directly into O-acyl-cyanohydrins using various anhydrides or acid chlorides in the presence of catalytic amounts of scandium(III) triflate. The reaction occurs with full retention of stereochemistry and allows the convenient measurement of enantiomeric excesses by chiral HPLC. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01200-5