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Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp(2))-H Alkylation

Sarkar, Rahul and Mukherjee, Santanu (2016) Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp(2))-H Alkylation. In: ORGANIC LETTERS, 18 (23). pp. 6160-6163.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.6b03168


The enantioselective Diels Alder (DA) reaction with monosubstituted p-benzoquinones is an unmet challenge. A new approach for the enantioselective synthesis of monosubstituted quinone-DA adducts is presented based on C(sp(2)) H alkylative desymmetrization of meso-DA adducts. Catalyzed by a tertiary amino-thiourea derivative, this reaction utilizes nitroalkanes as the alkylating agents and generates densely functionalized products bearing at least four contiguous stereogenic centers remote from the reaction site with excellent enantioselectivities.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 07 Jan 2017 10:15
Last Modified: 07 Jan 2017 10:15
URI: http://eprints.iisc.ac.in/id/eprint/55911

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