Graves Christopher R, Scheidt Karl A, Nguyen Sonbinh T
Department of Chemistry and Institute for Environmental Catalysis, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3313, USA.
Org Lett. 2006 Mar 16;8(6):1229-32. doi: 10.1021/ol060110w.
[reaction: see text] A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)Al(III)/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.
[反应：见正文] 据报道，(联萘酚)铝(III)/2-丙醇可对N-磷酰基酮亚胺进行高度对映选择性的 Meerwein-Schmidt-Ponndorf-Verley (MSPV) 还原反应。对于多种结构各异的酮亚胺，反应产率在79%至85%之间，对映体过量值较高（93%-98%）。为解释这种高选择性，提出了一种[2.0.4]双环螯合模型。
