ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

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.

[img] PDF
Tetrahed_75_3292-3298_2019.pdf - Published Version
Restricted to Registered users only

Download (707kB) | Request a copy
[img]
Preview
PDF
1-s2.0-S0040402019304612-mmc2.pdf - Published Supplemental Material

Download (3MB) | Preview
Official URL: http://doi.org/10.1016/j.tet.2019.04.049

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
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
Depositing User: Id for Latest eprints
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 View Item