Organocatalyzed Highly Enantioselective and anti-Selective Construction of γ-Butenolides through Vinylogous Mukaiyama Aldol Reaction

✍ Scribed by Ning Zhu; Bao-Chun Ma; Yong Zhang; Wei Wang

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 177 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201000099

✦ Synopsis

Abstract

The formation of chiral γ‐butenolides has been achieved with good yields (up to 90%), high enantioselectivity (up to 91%) and diastereoselectivity (up to 9/1, anti‐selective) through an organocatalyzed vinylogous Mukaiyama aldol reaction of 2‐(trimethylsilyloxy)furan and aldehydes. A wide range of chiral γ‐butenolides was obtained under mild conditions by this methodology.