Catalytic Enantioselective Synthesis of Diarylmethanols from Aryl Bromides and Aldehydes by Using Organolithium Reagents

✍ Scribed by Yuya Nakagawa; Yusuke Muramatsu; Toshiro Harada

• Book ID: 102173192
• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 379 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001254

✦ Synopsis

Abstract

A general method has been developed for preparing enantioenriched secondary alcohols by starting from aryl bromides and aldehydes. Aryl bromides were first treated with BuLi, and the resulting aryllithium reagents were mixed with titanium tetraisopropoxide and magnesium bromide. The reaction of aldehydes with the resulting mixed titanium reagents, in the presence of 3‐(3,5‐diphenylphenyl)‐H~8~‐BINOL (2 mol‐%) and titanium tetraisopropoxide, furnished the corresponding alcohols in high enantioselectivities and in high yields.