3-Substituted BINOL Schiff bases and their reductive products for catalytic asymmetric addition of diethylzinc to aldehydes

✍ Scribed by Bing Liu; Zhi-Bing Dong; Cao Fang; Hai-Bin Song; Jin-Shan Li

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 106 KB
• Volume: 20
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20559

✦ Synopsis

Abstract

Three new chiral 3‐substituted BINOL Schiff bases and their reductive 3‐arylaminomethyl BINOL products have been synthesized and used for the asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium tetraisopropoxide. The reaction provided optically active secondary alcohols in high yield (86–100%) and good enantioselectivity (up to 92% ee). Chirality, 2008. © 2008 Wiley‐Liss, Inc.