Synthesis of non-proteinogenic phenylalanine analogues by Suzuki cross-coupling of a serine-derived alkyl boronic acid

J E  Harvey; M N  Kenworthy; R J K  Taylor

doi:10.1016/j.tetlet.2003.12.154

Synthesis of non-proteinogenic phenylalanine analogues by Suzuki cross-coupling of a serine-derived alkyl boronic acid

J E Harvey, M N Kenworthy, R J K Taylor

Chemistry

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

Abstract

Protected serine-derived boronic acids have been prepared as beta-anionic alanine equivalents, and undergo efficient Suzuki cross-coupling with a variety of aryl halides to give, after elaboration, non-proteinogenic phenylalanine analogues. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2467-2471
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2003.12.154
Publication status	Published - 8 Mar 2004

Keywords

amino acid
Suzuki
cross-coupling
boronic acid
ALPHA-AMINO-ACIDS
ASPARTIC-ACID
STEREOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
ALKYLBORONIC ACIDS
ORGANIC HALIDES
DERIVATIVES
BETA
HYDROBORATION
REAGENTS

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10.1016/j.tetlet.2003.12.154

Cite this

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title = "Synthesis of non-proteinogenic phenylalanine analogues by Suzuki cross-coupling of a serine-derived alkyl boronic acid",

abstract = "Protected serine-derived boronic acids have been prepared as beta-anionic alanine equivalents, and undergo efficient Suzuki cross-coupling with a variety of aryl halides to give, after elaboration, non-proteinogenic phenylalanine analogues. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "amino acid, Suzuki, cross-coupling, boronic acid, ALPHA-AMINO-ACIDS, ASPARTIC-ACID, STEREOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, ALKYLBORONIC ACIDS, ORGANIC HALIDES, DERIVATIVES, BETA, HYDROBORATION, REAGENTS",

author = "Harvey, {J E} and Kenworthy, {M N} and Taylor, {R J K}",

year = "2004",

month = mar,

day = "8",

doi = "10.1016/j.tetlet.2003.12.154",

language = "English",

volume = "45",

pages = "2467--2471",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of non-proteinogenic phenylalanine analogues by Suzuki cross-coupling of a serine-derived alkyl boronic acid

AU - Harvey, J E

AU - Kenworthy, M N

AU - Taylor, R J K

PY - 2004/3/8

Y1 - 2004/3/8

N2 - Protected serine-derived boronic acids have been prepared as beta-anionic alanine equivalents, and undergo efficient Suzuki cross-coupling with a variety of aryl halides to give, after elaboration, non-proteinogenic phenylalanine analogues. (C) 2004 Elsevier Ltd. All rights reserved.

AB - Protected serine-derived boronic acids have been prepared as beta-anionic alanine equivalents, and undergo efficient Suzuki cross-coupling with a variety of aryl halides to give, after elaboration, non-proteinogenic phenylalanine analogues. (C) 2004 Elsevier Ltd. All rights reserved.

KW - amino acid

KW - Suzuki

KW - cross-coupling

KW - boronic acid

KW - ALPHA-AMINO-ACIDS

KW - ASPARTIC-ACID

KW - STEREOSELECTIVE SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - ALKYLBORONIC ACIDS

KW - ORGANIC HALIDES

KW - DERIVATIVES

KW - BETA

KW - HYDROBORATION

KW - REAGENTS

U2 - 10.1016/j.tetlet.2003.12.154

DO - 10.1016/j.tetlet.2003.12.154

M3 - Article

SN - 0040-4039

VL - 45

SP - 2467

EP - 2471

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -