NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION

K  GOODALL; A F  PARSONS

NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION

Chemistry

Research output: Contribution to journal › Comment/debate › peer-review

Abstract

The tributyltin hydride mediated radical cyclisation of N-(alpha-chloroacetamido)dehydroalanine derivatives prepared from serine proceeds regioselectively to give pyroglutamates in 47-74% yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured' 5-endo-trig manner.

Original language	English
Pages (from-to)	3257-3259
Number of pages	3
Journal	Journal of the Chemical Society-Perkin Transactions 1
Issue number	22
Publication status	Published - 21 Nov 1994

Keywords

ASYMMETRIC-SYNTHESIS
5-MEMBERED LACTAMS
CYCLIZATION
ACID
(-)-TRACHELANTHAMIDINE
ANALOGS
PYRROLIDINES
TEMPERATURE
5-ENDO-TRIG
ESTERS

Cite this

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title = "NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION",

abstract = "The tributyltin hydride mediated radical cyclisation of N-(alpha-chloroacetamido)dehydroalanine derivatives prepared from serine proceeds regioselectively to give pyroglutamates in 47-74% yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured' 5-endo-trig manner.",

keywords = "ASYMMETRIC-SYNTHESIS, 5-MEMBERED LACTAMS, CYCLIZATION, ACID, (-)-TRACHELANTHAMIDINE, ANALOGS, PYRROLIDINES, TEMPERATURE, 5-ENDO-TRIG, ESTERS",

author = "K GOODALL and PARSONS, {A F}",

year = "1994",

month = nov,

day = "21",

language = "English",

pages = "3257--3259",

journal = "Journal of the Chemical Society-Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "22",

}

TY - JOUR

T1 - NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION

AU - GOODALL, K

AU - PARSONS, A F

PY - 1994/11/21

Y1 - 1994/11/21

N2 - The tributyltin hydride mediated radical cyclisation of N-(alpha-chloroacetamido)dehydroalanine derivatives prepared from serine proceeds regioselectively to give pyroglutamates in 47-74% yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured' 5-endo-trig manner.

AB - The tributyltin hydride mediated radical cyclisation of N-(alpha-chloroacetamido)dehydroalanine derivatives prepared from serine proceeds regioselectively to give pyroglutamates in 47-74% yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured' 5-endo-trig manner.

KW - ASYMMETRIC-SYNTHESIS

KW - 5-MEMBERED LACTAMS

KW - CYCLIZATION

KW - ACID

KW - (-)-TRACHELANTHAMIDINE

KW - ANALOGS

KW - PYRROLIDINES

KW - TEMPERATURE

KW - 5-ENDO-TRIG

KW - ESTERS

M3 - Comment/debate

SN - 0300-922X

SP - 3257

EP - 3259

JO - Journal of the Chemical Society-Perkin Transactions 1

JF - Journal of the Chemical Society-Perkin Transactions 1

IS - 22

ER -