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

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

16 Scopus citations

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
State	Published - 7 Aug 2020
Externally published	Yes

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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.",

year = "2020",

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

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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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U2 - 10.1021/acs.orglett.0c02071

DO - 10.1021/acs.orglett.0c02071

M3 - 文章

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AN - SCOPUS:85088858367

SN - 1523-7060

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SP - 5978

EP - 5983

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

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

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