Enantioselective 4+2]-Annulation of Azlactones with Copper-Allenylidenes under Cooperative Catalysis: Synthesis of alpha-Quaternary alpha-Acylaminoamides

Simlandy, Amit Kumar and Ghosh, Biki and Mukherjee, Santanu (2019) Enantioselective 4+2]-Annulation of Azlactones with Copper-Allenylidenes under Cooperative Catalysis: Synthesis of alpha-Quaternary alpha-Acylaminoamides. In: ORGANIC LETTERS, 21 (9). pp. 3361-3366.

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Abstract

The first enantioselective decarboxylative 4 + 2]-annulation of ethynyl benzoxazinanones with azlactones has been developed under cooperative copper and bifunctional tertiary aminourea catalysis. This direct and modular approach combines dipolar copper-allenylidene intermediates with azlactone enolates and allows for the synthesis of alpha-quaternary alpha-acylaminoamides as a single diastereomer generally in high yields with good to excellent enantioselectivities (up to 99:1 er).

Item Type:	Journal Article
Publication:	ORGANIC LETTERS
Publisher:	AMER CHEMICAL SOC
Additional Information:	copyright for this article belongs to ORGANIC LETTERS
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	24 Jun 2019 18:11
Last Modified:	24 Jun 2019 18:11
URI:	http://eprints.iisc.ac.in/id/eprint/63066

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