Enantioselective Formal C(sp2)−H Vinylation

Madhu Sudan Manna; Rahul Sarkar; Santanu Mukherjee

doi:10.1002/chem.201602253

Enantioselective Formal C(sp²)−H Vinylation

Madhu Sudan Manna, Rahul Sarkar, Santanu Mukherjee

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

24 Scopus citations

Abstract

An enantioselective formal C(sp²)−H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.

Original language	English (US)
Pages (from-to)	14912-14919
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	42
DOIs	https://doi.org/10.1002/chem.201602253
State	Published - Oct 10 2016
Externally published	Yes

Keywords

C−H functionalization
decarboxylation
desymmetrization
lactones
vinylation

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201602253

Cite this

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title = "Enantioselective Formal C(sp2)−H Vinylation",

abstract = "An enantioselective formal C(sp2)−H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.",

keywords = "C−H functionalization, decarboxylation, desymmetrization, lactones, vinylation",

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AU - Sarkar, Rahul

AU - Mukherjee, Santanu

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N2 - An enantioselective formal C(sp2)−H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.

AB - An enantioselective formal C(sp2)−H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.

KW - C−H functionalization

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KW - desymmetrization

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KW - vinylation

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