Control of enantioselectivity through a hydrogen-bonded template in the vanadium(V)-catalyzed epoxidation of allylic alcohols by optically active hydroperoxides
作者:Waldemar Adam、Albert K. Beck、Arkadius Pichota、Chantu R. Saha-Möller、Dieter Seebach、Nadine Vogl、Rui Zhang
DOI:10.1016/s0957-4166(03)00213-1
日期:2003.5
The vanadiuin(V)-catalyzed asymmetric epoxidation of primary allylic alcohols by the optically active TADDOL-derived hydroperoxide as the asymmetric controller provides the corresponding (R)-epoxides in up to 72% ee. From this mechanistic study we conclude that this novel enantioselective oxygen transfer takes place via a hydrogen-bonded template, held together by the vanadium metal. (C) 2003 Elsevier Science Ltd. All rights reserved.
CXXIV.—A new synthesis of phthalimidoacetonitriles and a note on aminoacetonitrile sulphates