Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction

Harish Kumar Potukuchi; Thorsten Bach

doi:10.1021/jo402107m

Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction

Harish Kumar Potukuchi, Thorsten Bach

Chair of Organic Chemistry 1

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51 Scopus citations

Abstract

A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds without racemization at the stereogenic center of the amino acid.

Original language	English
Pages (from-to)	12263-12267
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	78
Issue number	23
DOIs	https://doi.org/10.1021/jo402107m
State	Published - 6 Dec 2013

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title = "Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction",

abstract = "A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds without racemization at the stereogenic center of the amino acid.",

author = "Potukuchi, {Harish Kumar} and Thorsten Bach",

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AU - Potukuchi, Harish Kumar

AU - Bach, Thorsten

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Y1 - 2013/12/6

N2 - A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds without racemization at the stereogenic center of the amino acid.

AB - A palladium(II)-catalyzed norbornene-mediated regioselective alkylation at the C-2 indole position of N-tert-butyloxycarbonyl (Boc)-protected (S)-tryptophan ethyl ester is reported. The protocol employs mild reaction conditions and is tolerant of a range of functional groups. The reaction proceeds without racemization at the stereogenic center of the amino acid.

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U2 - 10.1021/jo402107m

DO - 10.1021/jo402107m

M3 - Article

C2 - 24237413

AN - SCOPUS:84890178764

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SP - 12263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction

Abstract

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