Catalytic Asymmetric Direct Vinylogous Michael Addition of Deconjugated Butenolides to Maleimides for the Construction of Quaternary Stereogenic Centers

Manna, Madhu Sudan and Mukherjee, Santanu (2012) Catalytic Asymmetric Direct Vinylogous Michael Addition of Deconjugated Butenolides to Maleimides for the Construction of Quaternary Stereogenic Centers. In: CHEMISTRY-A EUROPEAN JOURNAL, 18 (48). pp. 15277-15282.

	PDF che-A_eur_jol_18-48_15277_2012.pdf - Published Version Restricted to Registered users only Download (559kB) | Request a copy
	PDF chem_201203180_sm_miscellaneous_information.pdf - Published Supplemental Material Restricted to Registered users only Download (7MB) | Request a copy

Abstract

Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

Item Type:	Journal Article
Publication:	CHEMISTRY-A EUROPEAN JOURNAL
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copyright for this article belongs to WILEY-V C H VERLAG GMBH, GERMANY
Keywords:	asymmetric catalysis;butyrolactone;maleimide;Michael addition;thiourea
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	02 Jan 2013 07:49
Last Modified:	02 Jan 2013 07:49
URI:	http://eprints.iisc.ac.in/id/eprint/45588

Actions (login required)

View Item