Organocatalytic enantioselective formal C(sp2)-H alkylation

Madhu Sudan Manna; Santanu Mukherjee

doi:10.1021/ja5117556

Organocatalytic enantioselective formal C(sp²)-H alkylation

Madhu Sudan Manna, Santanu Mukherjee

Research output: Contribution to journal › Article › peer-review

85 Scopus citations

Abstract

An organocatalytic enantioselective formal C(sp²)-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.

Original language	English (US)
Pages (from-to)	130-133
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	1
DOIs	https://doi.org/10.1021/ja5117556
State	Published - Jan 14 2015
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja5117556

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abstract = "An organocatalytic enantioselective formal C(sp2)-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.",

author = "Manna, {Madhu Sudan} and Santanu Mukherjee",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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AB - An organocatalytic enantioselective formal C(sp2)-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.

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Organocatalytic enantioselective formal C(sp²)-H alkylation

Abstract

ASJC Scopus subject areas

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