Synthesis of 2,3-Fused Indoline Aminals via 4 + 2 Cycloaddition of NH-free Benzazetidines with Indoles

Zibo Bai; Huarong Tong; Hao Wang; Gong Chen; Gang He

doi:10.1002/cjoc.201800483

Synthesis of 2,3-Fused Indoline Aminals via 4 + 2 Cycloaddition of NH-free Benzazetidines with Indoles

Zibo Bai
, Huarong Tong
, Hao Wang
, Gong Chen
, Gang He

Chemistry

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

16 Scopus citations

Abstract

A 4 + 2 cycloaddition reaction of NH-free benzazetidines with indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and indoles, and offers a convenient method for stereoselective synthesis of various cis-2,3-fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.

Original language	English (US)
Pages (from-to)	119-125
Number of pages	7
Journal	Chinese Journal of Chemistry
Volume	37
Issue number	2
DOIs	https://doi.org/10.1002/cjoc.201800483
State	Published - Feb 1 2019

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1002/cjoc.201800483

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title = "Synthesis of 2,3-Fused Indoline Aminals via 4 + 2 Cycloaddition of NH-free Benzazetidines with Indoles",

abstract = "A 4 + 2 cycloaddition reaction of NH-free benzazetidines with indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and indoles, and offers a convenient method for stereoselective synthesis of various cis-2,3-fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.",

author = "Zibo Bai and Huarong Tong and Hao Wang and Gong Chen and Gang He",

note = "Funding Information: We greatly thank the National Natural Science Foundation of China (Nos. 21502098, 21672105), the Natural Science Foundation of Tianjin (17JCYBJC19700), the Qindao National Laboratory for Marine Science and Technology, and the State Key Laboratory of Elemento-Organic Chemistry at Nankai University for financial support of this work. Publisher Copyright: {\textcopyright} 2019 SIOC, CAS, Shanghai, \& WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/cjoc.201800483",

language = "English (US)",

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TY - JOUR

T1 - Synthesis of 2,3-Fused Indoline Aminals via 4 + 2 Cycloaddition of NH-free Benzazetidines with Indoles

AU - Bai, Zibo

AU - Tong, Huarong

AU - Wang, Hao

AU - Chen, Gong

AU - He, Gang

N1 - Funding Information: We greatly thank the National Natural Science Foundation of China (Nos. 21502098, 21672105), the Natural Science Foundation of Tianjin (17JCYBJC19700), the Qindao National Laboratory for Marine Science and Technology, and the State Key Laboratory of Elemento-Organic Chemistry at Nankai University for financial support of this work. Publisher Copyright: © 2019 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/2/1

Y1 - 2019/2/1

N2 - A 4 + 2 cycloaddition reaction of NH-free benzazetidines with indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and indoles, and offers a convenient method for stereoselective synthesis of various cis-2,3-fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.

AB - A 4 + 2 cycloaddition reaction of NH-free benzazetidines with indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and indoles, and offers a convenient method for stereoselective synthesis of various cis-2,3-fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.

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UR - https://www.scopus.com/pages/publications/85059103469#tab=citedBy

U2 - 10.1002/cjoc.201800483

DO - 10.1002/cjoc.201800483

M3 - Article

AN - SCOPUS:85059103469

SN - 1001-604X

VL - 37

SP - 119

EP - 125

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 2

ER -

Synthesis of 2,3-Fused Indoline Aminals via 4 + 2 Cycloaddition of NH-free Benzazetidines with Indoles

Abstract

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