Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with α,β-unsaturated aldehydes: An easy access to 2-substituted indoles

Liang Hong; Chunxia Liu; Wangsheng Sun; Lei Wang; Kwok Yin Wong; Rui Wang

doi:10.1021/ol900461v

Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with α,β-unsaturated aldehydes: An easy access to 2-substituted indoles

Liang Hong
, Chunxia Liu
, Wangsheng Sun
, Lei Wang
, Kwok Yin Wong
, Rui Wang

Research output: Journal article publication › Journal article › Academic research › peer-review

88 Citations (Scopus)

Abstract

An enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles and α,β-unsaturated aldehydes has been developed. The process is promoted by diphenylprolinol ether to afford 2-substituted 4,7-dihydroindoles in high yields and enantioselectivities. After a subsequent oxidation of the products, the optically active 2-substituted indoles could be obtained smoothly in high yields without any loss of enantioselectivity.

Original language	English
Pages (from-to)	2177-2180
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	10
DOIs	https://doi.org/10.1021/ol900461v
Publication status	Published - 21 May 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900461v

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title = "Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with α,β-unsaturated aldehydes: An easy access to 2-substituted indoles",

abstract = "An enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles and α,β-unsaturated aldehydes has been developed. The process is promoted by diphenylprolinol ether to afford 2-substituted 4,7-dihydroindoles in high yields and enantioselectivities. After a subsequent oxidation of the products, the optically active 2-substituted indoles could be obtained smoothly in high yields without any loss of enantioselectivity.",

author = "Liang Hong and Chunxia Liu and Wangsheng Sun and Lei Wang and Wong, \{Kwok Yin\} and Rui Wang",

year = "2009",

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journal = "Organic Letters",

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Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with α,β-unsaturated aldehydes: An easy access to 2-substituted indoles. / Hong, Liang; Liu, Chunxia; Sun, Wangsheng et al.
In: Organic Letters, Vol. 11, No. 10, 21.05.2009, p. 2177-2180.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

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AU - Hong, Liang

AU - Liu, Chunxia

AU - Sun, Wangsheng

AU - Wang, Lei

AU - Wong, Kwok Yin

AU - Wang, Rui

PY - 2009/5/21

Y1 - 2009/5/21

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AB - An enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles and α,β-unsaturated aldehydes has been developed. The process is promoted by diphenylprolinol ether to afford 2-substituted 4,7-dihydroindoles in high yields and enantioselectivities. After a subsequent oxidation of the products, the optically active 2-substituted indoles could be obtained smoothly in high yields without any loss of enantioselectivity.

UR - https://www.scopus.com/pages/publications/66149124445

U2 - 10.1021/ol900461v

DO - 10.1021/ol900461v

M3 - Journal article

C2 - 19385607

SN - 1523-7060

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ER -

Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with α,β-unsaturated aldehydes: An easy access to 2-substituted indoles

Abstract

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