Decarboxylation-based traceless linking with aroyl acrylic acids

John Nielsen

doi:10.1016/S0040-4039(98)00176-2

Decarboxylation-based traceless linking with aroyl acrylic acids

John Nielsen

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Abstract

beta-Keto carboxylic acids are known to decarboxylate readily. In our pursuit to synthesize beta-indolinyl propiophenones, we have exploited this chemistry as a mean of establishing a traceless handle. 2-Aroyl acrylic acids have been esterified to a trityl resin, after which Michael-type addition of indolines have been performed. Upon cleavage, the products are decarboxylated, and the beta-indolinyl propiophenones are isolated. The reaction conditions have been optimized, and a small library has been prepared. (C) 1998 Elsevier Science Ltd. All rights reserved.

Original language	English
Journal	Tetrahedron Letters
Volume	39
Issue number	15
Pages (from-to)	2207-2210
ISSN	0040-4039
DOIs	https://doi.org/10.1016/S0040-4039(98)00176-2
Publication status	Published - 1998

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title = "Decarboxylation-based traceless linking with aroyl acrylic acids",

abstract = "beta-Keto carboxylic acids are known to decarboxylate readily. In our pursuit to synthesize beta-indolinyl propiophenones, we have exploited this chemistry as a mean of establishing a traceless handle. 2-Aroyl acrylic acids have been esterified to a trityl resin, after which Michael-type addition of indolines have been performed. Upon cleavage, the products are decarboxylated, and the beta-indolinyl propiophenones are isolated. The reaction conditions have been optimized, and a small library has been prepared. (C) 1998 Elsevier Science Ltd. All rights reserved. ",

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AU - Nielsen, John

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N2 - beta-Keto carboxylic acids are known to decarboxylate readily. In our pursuit to synthesize beta-indolinyl propiophenones, we have exploited this chemistry as a mean of establishing a traceless handle. 2-Aroyl acrylic acids have been esterified to a trityl resin, after which Michael-type addition of indolines have been performed. Upon cleavage, the products are decarboxylated, and the beta-indolinyl propiophenones are isolated. The reaction conditions have been optimized, and a small library has been prepared. (C) 1998 Elsevier Science Ltd. All rights reserved.

AB - beta-Keto carboxylic acids are known to decarboxylate readily. In our pursuit to synthesize beta-indolinyl propiophenones, we have exploited this chemistry as a mean of establishing a traceless handle. 2-Aroyl acrylic acids have been esterified to a trityl resin, after which Michael-type addition of indolines have been performed. Upon cleavage, the products are decarboxylated, and the beta-indolinyl propiophenones are isolated. The reaction conditions have been optimized, and a small library has been prepared. (C) 1998 Elsevier Science Ltd. All rights reserved.

U2 - 10.1016/S0040-4039(98)00176-2

DO - 10.1016/S0040-4039(98)00176-2

M3 - Journal article

VL - 39

SP - 2207

EP - 2210

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 15

ER -

Decarboxylation-based traceless linking with aroyl acrylic acids

Abstract

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