Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

Shangbin Jin; Chenguang Li; Yuanhui Ma; Yuhe Kan; Yong Jian Zhang; Wanbin Zhang

doi:10.1039/c0ob00016g

Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

Shangbin Jin
, Chenguang Li
, Yuanhui Ma
, Yuhe Kan
, Yong Jian Zhang
, Wanbin Zhang

Shanghai Jiao Tong University
Huaiyin Normal University

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

30 Scopus citations

Abstract

The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89%) with high levels of enantioselectivity (80-93% ee) using only 2 mol% of catalyst loading.

Original language	English
Pages (from-to)	4011-4015
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	17
DOIs	https://doi.org/10.1039/c0ob00016g
State	Published - 7 Sep 2010
Externally published	Yes

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title = "Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes",

abstract = "The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89\%) with high levels of enantioselectivity (80-93\% ee) using only 2 mol\% of catalyst loading.",

author = "Shangbin Jin and Chenguang Li and Yuanhui Ma and Yuhe Kan and Zhang, \{Yong Jian\} and Wanbin Zhang",

year = "2010",

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T1 - Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

AU - Jin, Shangbin

AU - Li, Chenguang

AU - Ma, Yuanhui

AU - Kan, Yuhe

AU - Zhang, Yong Jian

AU - Zhang, Wanbin

PY - 2010/9/7

Y1 - 2010/9/7

N2 - The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89%) with high levels of enantioselectivity (80-93% ee) using only 2 mol% of catalyst loading.

AB - The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89%) with high levels of enantioselectivity (80-93% ee) using only 2 mol% of catalyst loading.

UR - https://www.scopus.com/pages/publications/77955498194

U2 - 10.1039/c0ob00016g

DO - 10.1039/c0ob00016g

M3 - 文章

AN - SCOPUS:77955498194

SN - 1477-0520

VL - 8

SP - 4011

EP - 4015

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

Abstract

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