Asymmetric Organocatalytic Michael Addition–Cyclization Cascade Reaction of Nitroalkanes with o-Hydroxycinnamaldehydes

✍ Scribed by Kwang-Su Choi; Sung-Gon Kim

• Book ID: 102173260
• Publisher: John Wiley and Sons
• Year: 2012
• Tongue: English
• Weight: 463 KB
• Volume: 2012
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101794

✦ Synopsis

Abstract

A catalytic enantioselective Michael addition–cyclization reaction of nitroalkanes with o‐hydroxycinnamaldehydes has been established by using a diphenylprolinol TMS ether as an organocatalyst. The reaction afforded the corresponding 4‐substituted chroman‐2‐ols in excellent yields with high levels of enantioselectivities (95 to >99 % ee).