A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramlecular Hetero-Michael Reaction of alpha,beta-Unsaturated Carboxylic Acids

作者：Azuma Takumi; Murata Akihiro; Kobayashi Yusuke; Inokuma Tsubasa; Takemoto Yoshiji^*

来源：Organic Letters, 2014, 16(16): 4256-4259.

DOI：10.1021/ol501954r

A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of alpha,beta-unsaturated carboxylic acids. The combination of an arylboronic add with a chiral aminothiourea allowed for these reactions to proceed successfully in an enantioselective manner to afford the desired heterocycles in high yields and ee%26apos;s (up to 96% ee). The overall utility of this dual catalytic system was demonstrated by a one-pot enantioselective synthesis of (+)-erythrococcamide B, which proceeded via sequential Michael and amidation reactions.

• 出版日期2014-8-15