A Selective Transformation of Enals into Chiral gamma-Amino Alcohols

作者:Calow Adam D J; Batsanov Andrei S; Pujol Alba; Sole Cristina; Fernandez Elena*; Whiting Andrew
来源:Organic Letters, 2013, 15(18): 4810-4813.
DOI:10.1021/ol4022029

摘要

A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.

  • 出版日期2013-9-20