Umpolung of donor-acceptor cyclopropanes: Via N-heterocyclic carbene organic catalysis

Guihua Nie; Xuan Huang; Zhongyao Wang; Dingwu Pan; Junmin Zhang; Yonggui Robin Chi

doi:10.1039/d1qo00826a

Umpolung of donor-acceptor cyclopropanes: Via N-heterocyclic carbene organic catalysis

Guihua Nie, Xuan Huang, Zhongyao Wang, Dingwu Pan, Junmin Zhang, Yonggui Robin Chi^*

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities.

Original language	English
Pages (from-to)	5105-5111
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	8
Issue number	18
DOIs	https://doi.org/10.1039/d1qo00826a
Publication status	Published - Sept 21 2021
Externally published	Yes

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Publisher Copyright:
© 2021 the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

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title = "Umpolung of donor-acceptor cyclopropanes: Via N-heterocyclic carbene organic catalysis",

abstract = "A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities.",

author = "Guihua Nie and Xuan Huang and Zhongyao Wang and Dingwu Pan and Junmin Zhang and Chi, {Yonggui Robin}",

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month = sep,

day = "21",

doi = "10.1039/d1qo00826a",

language = "English",

volume = "8",

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TY - JOUR

T1 - Umpolung of donor-acceptor cyclopropanes

T2 - Via N-heterocyclic carbene organic catalysis

AU - Nie, Guihua

AU - Huang, Xuan

AU - Wang, Zhongyao

AU - Pan, Dingwu

AU - Zhang, Junmin

AU - Chi, Yonggui Robin

PY - 2021/9/21

Y1 - 2021/9/21

N2 - A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities.

AB - A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities.

UR - http://www.scopus.com/inward/record.url?scp=85115190272&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85115190272&partnerID=8YFLogxK

U2 - 10.1039/d1qo00826a

DO - 10.1039/d1qo00826a

M3 - Article

AN - SCOPUS:85115190272

SN - 2052-4110

VL - 8

SP - 5105

EP - 5111

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 18

ER -

Umpolung of donor-acceptor cyclopropanes: Via N-heterocyclic carbene organic catalysis

Abstract

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