Sidearm effect: improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates

Jian Zhou; Yong Tang

doi:10.1021/ja026936k

Sidearm effect: improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates

J Am Chem Soc. 2002 Aug 7;124(31):9030-1. doi: 10.1021/ja026936k.

Authors

Jian Zhou¹, Yong Tang

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai, China.

PMID: 12148989
DOI: 10.1021/ja026936k

Abstract

A pseudo-C3-trisoxazoline was designed and synthesized. The improvement of the traditional bisoxazoline into a novel trisoxazoline by a sidearm approach resulted in highly catalytic enantioselective Michael addition of indoles to alkylidene malonates. Excellent catalytic reactivity and enantioselectivity (up to 99% yield and 93% ee) were achieved.