Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

Pan Guo; Wangbin Sun; Yu Liu; Yong Xin Li; Teck Peng Loh; Yaojia Jiang

doi:10.1021/acs.orglett.0c02071

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

Pan Guo, Wangbin Sun, Yu Liu, Yong Xin Li, Teck Peng Loh^*, Yaojia Jiang^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

Original language	English
Pages (from-to)	5978-5983
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.0c02071
Publication status	Published - Aug 7 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c02071

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title = "Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy",

abstract = "A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.",

author = "Pan Guo and Wangbin Sun and Yu Liu and Li, \{Yong Xin\} and Loh, \{Teck Peng\} and Yaojia Jiang",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.orglett.0c02071",

language = "English",

volume = "22",

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T1 - Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

AU - Guo, Pan

AU - Sun, Wangbin

AU - Liu, Yu

AU - Li, Yong Xin

AU - Loh, Teck Peng

AU - Jiang, Yaojia

PY - 2020/8/7

Y1 - 2020/8/7

N2 - A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

AB - A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

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EP - 5983

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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