Radical reactions leading to substituted pyroglutamates

S R  Baker; A F  Parsons; M  Wilson

Radical reactions leading to substituted pyroglutamates

S R Baker, A F Parsons, M Wilson

Chemistry

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

Abstract

The Bu3SnH mediated cyclisation of a serine-derived dehydroalanine was shown to provide an efficient approach to a protected 4-phenylpyroglutamate which was elaborated to 4-phenylglutamic acid in good yield. Cyclisation reactions of this type were shown to proceed via an intermediate captodative radical which could be trapped intermolecularly using an alkene e.g. styrene or methyl methacrylate. This method has potential for the synthesis of various 4- and/or 2-substituted glutamic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2815-2818
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	18
Publication status	Published - 30 Apr 1998

Keywords

ATOM TRANSFER CYCLIZATION
GAMMA-LACTAMS
N-ALLYLTRICHLOROACETAMIDES
5-MEMBERED LACTAMS
ORGANIC-SYNTHESIS
ROUTE
ACID
(-)-TRACHELANTHAMIDINE
PYRROLIDINONES
TEMPERATURE

Cite this

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title = "Radical reactions leading to substituted pyroglutamates",

abstract = "The Bu3SnH mediated cyclisation of a serine-derived dehydroalanine was shown to provide an efficient approach to a protected 4-phenylpyroglutamate which was elaborated to 4-phenylglutamic acid in good yield. Cyclisation reactions of this type were shown to proceed via an intermediate captodative radical which could be trapped intermolecularly using an alkene e.g. styrene or methyl methacrylate. This method has potential for the synthesis of various 4- and/or 2-substituted glutamic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.",

keywords = "ATOM TRANSFER CYCLIZATION, GAMMA-LACTAMS, N-ALLYLTRICHLOROACETAMIDES, 5-MEMBERED LACTAMS, ORGANIC-SYNTHESIS, ROUTE, ACID, (-)-TRACHELANTHAMIDINE, PYRROLIDINONES, TEMPERATURE",

author = "Baker, {S R} and Parsons, {A F} and M Wilson",

year = "1998",

month = apr,

day = "30",

language = "English",

volume = "39",

pages = "2815--2818",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "18",

}

TY - JOUR

T1 - Radical reactions leading to substituted pyroglutamates

AU - Baker, S R

AU - Parsons, A F

AU - Wilson, M

PY - 1998/4/30

Y1 - 1998/4/30

N2 - The Bu3SnH mediated cyclisation of a serine-derived dehydroalanine was shown to provide an efficient approach to a protected 4-phenylpyroglutamate which was elaborated to 4-phenylglutamic acid in good yield. Cyclisation reactions of this type were shown to proceed via an intermediate captodative radical which could be trapped intermolecularly using an alkene e.g. styrene or methyl methacrylate. This method has potential for the synthesis of various 4- and/or 2-substituted glutamic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

AB - The Bu3SnH mediated cyclisation of a serine-derived dehydroalanine was shown to provide an efficient approach to a protected 4-phenylpyroglutamate which was elaborated to 4-phenylglutamic acid in good yield. Cyclisation reactions of this type were shown to proceed via an intermediate captodative radical which could be trapped intermolecularly using an alkene e.g. styrene or methyl methacrylate. This method has potential for the synthesis of various 4- and/or 2-substituted glutamic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

KW - ATOM TRANSFER CYCLIZATION

KW - GAMMA-LACTAMS

KW - N-ALLYLTRICHLOROACETAMIDES

KW - 5-MEMBERED LACTAMS

KW - ORGANIC-SYNTHESIS

KW - ROUTE

KW - ACID

KW - (-)-TRACHELANTHAMIDINE

KW - PYRROLIDINONES

KW - TEMPERATURE

M3 - Article

SN - 0040-4039

VL - 39

SP - 2815

EP - 2818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -