Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones

Andrew C Silvanus; Stephen J Heffernan; D J Liptrot; Gabriele Kociok-Kohn; B I Andrews; David R Carbery

doi:10.1021/ol900014a

Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones

Andrew C Silvanus, Stephen J Heffernan, D J Liptrot, Gabriele Kociok-Kohn, B I Andrews, David R Carbery

Department of Chemistry

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

43 Citations (SciVal)

Abstract

A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic Indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction Is also seen to be sensitive to substrate structure and catalyst.

Original language	English
Pages (from-to)	1175-1178
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	5
Early online date	11 Feb 2009
DOIs	https://doi.org/10.1021/ol900014a
Publication status	Published - 5 Mar 2009

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10.1021/ol900014a

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title = "Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones",

abstract = "A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic Indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction Is also seen to be sensitive to substrate structure and catalyst.",

author = "Silvanus, \{Andrew C\} and Heffernan, \{Stephen J\} and Liptrot, \{D J\} and Gabriele Kociok-Kohn and Andrews, \{B I\} and Carbery, \{David R\}",

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T1 - Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones

AU - Silvanus, Andrew C

AU - Heffernan, Stephen J

AU - Liptrot, D J

AU - Kociok-Kohn, Gabriele

AU - Andrews, B I

AU - Carbery, David R

PY - 2009/3/5

Y1 - 2009/3/5

N2 - A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic Indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction Is also seen to be sensitive to substrate structure and catalyst.

AB - A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic Indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction Is also seen to be sensitive to substrate structure and catalyst.

UR - https://www.scopus.com/pages/publications/64349087238

UR - http://dx.doi.org/10.1021/ol900014a

U2 - 10.1021/ol900014a

DO - 10.1021/ol900014a

M3 - Article

SN - 1523-7060

VL - 11

SP - 1175

EP - 1178

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones

Abstract

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