NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION

Authors
GOODALL K PARSONS AF
Citation
K. Goodall et Af. Parsons, NEW ROUTE TO PYROGLUTAMATES VIA ALPHA-CHLORO AMIDE RADICAL CYCLIZATION, Journal of the Chemical Society. Perkin transactions. I, (22), 1994, pp. 3257-3259
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
22
Year of publication
1994
Pages
3257 - 3259
Database
ISI
SICI code
0300-922X(1994):22<3257:NRTPVA>2.0.ZU;2-Y
Abstract
The tributyltin hydride mediated radical cyclisation of N-(alpha-chlor oacetamido)dehydroalanine derivatives prepared from serine proceeds re gioselectively to give pyroglutamates in 47-74% yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured ' 5-endo-trig manner.