A diastereoselective radical cyclisation approach to pyroglutamates

K  Goodall; A F  Parsons

A diastereoselective radical cyclisation approach to pyroglutamates

Chemistry

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

Abstract

The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd

Original language	English
Pages (from-to)	491-494
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	3
Publication status	Published - 20 Jan 1997

Keywords

ALPHA-AMINO-ACIDS
ASYMMETRIC INDUCTION
ENANTIOSELECTIVE SYNTHESES
LEWIS-ACID
CYCLIZATION
ESTERS
DEHYDROALANINE
AMIDES
STEREOSELECTIVITY
ORGANOBORANES

Cite this

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title = "A diastereoselective radical cyclisation approach to pyroglutamates",

abstract = "The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd",

keywords = "ALPHA-AMINO-ACIDS, ASYMMETRIC INDUCTION, ENANTIOSELECTIVE SYNTHESES, LEWIS-ACID, CYCLIZATION, ESTERS, DEHYDROALANINE, AMIDES, STEREOSELECTIVITY, ORGANOBORANES",

author = "K Goodall and Parsons, {A F}",

year = "1997",

month = jan,

day = "20",

language = "English",

volume = "38",

pages = "491--494",

journal = "Tetrahedron Letters",

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T1 - A diastereoselective radical cyclisation approach to pyroglutamates

AU - Goodall, K

AU - Parsons, A F

PY - 1997/1/20

Y1 - 1997/1/20

N2 - The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd

AB - The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd

KW - ALPHA-AMINO-ACIDS

KW - ASYMMETRIC INDUCTION

KW - ENANTIOSELECTIVE SYNTHESES

KW - LEWIS-ACID

KW - CYCLIZATION

KW - ESTERS

KW - DEHYDROALANINE

KW - AMIDES

KW - STEREOSELECTIVITY

KW - ORGANOBORANES

M3 - Article

SN - 0040-4039

VL - 38

SP - 491

EP - 494

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -