Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides

Ray, Bidisha and Mukherjee, Santanu (2019) Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides. In: TETRAHEDRON, 75 (24). pp. 3292-3298.

	PDF Tetrahed_75_3292-3298_2019.pdf - Published Version Restricted to Registered users only Download (707kB) | Request a copy
Preview	PDF 1-s2.0-S0040402019304612-mmc2.pdf - Published Supplemental Material Download (3MB) | Preview

Abstract

The first catalytic enantioselective Michael addition of deconjugated butyrolactams to N-arylmaleimides is developed with the help of a bifunctional tertiary aminosquaramide catalyst. Unlike the widely explored and structurally related vinylogous nucleophile - deconjugated butenolides, deconjugated butyrolactams are found to be exclusively alpha-selective. The resulting highly substituted and densely functionalized products, bearing contiguous all-carbon quaternary and tertiary stereocenters, are formed in good yields with moderate diastereoselectivity and good to excellent enantioselectivity (up to 99:1 er).

Item Type:	Journal Article
Publication:	TETRAHEDRON
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Additional Information:	copyright of this article belongs to PERGAMON-ELSEVIER SCIENCE LTD
Keywords:	Michael addition; Butyrolactam; Maleimide; All-carbon quaternary stereocenter; Bifunctional catalysis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	01 Jul 2019 12:03
Last Modified:	01 Jul 2019 12:03
URI:	http://eprints.iisc.ac.in/id/eprint/63123

Actions (login required)

View Item