Stereoselective synthesis of alpha-methyl and beta-methyl pyrrolidine 5,5-trans-lactam (5-oxo-hexahydro-pyrrolo[3,2-b]pyrrole) and stereoselective alkylation of the strained pyrrolidine 5,5-trans-lactam ring system

Authors
Borthwick, AD Crame, AJ Davies, DE Exall, AM Jackson, DL Mason, AM Pennell, AMK Weingarten, GG
Citation
Ad. Borthwick et al., Stereoselective synthesis of alpha-methyl and beta-methyl pyrrolidine 5,5-trans-lactam (5-oxo-hexahydro-pyrrolo[3,2-b]pyrrole) and stereoselective alkylation of the strained pyrrolidine 5,5-trans-lactam ring system, SYNLETT, (4), 2000, pp. 504-508
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
4
Year of publication
2000
Pages
504 - 508
Database
ISI
SICI code
0936-5214(200004):4<504:SSOAAB>2.0.ZU;2-G
Abstract
The alpha-methyl pyrrolidine 5,5-trans-lactam 11 was prepared by stereosele ctive alkylation of the strained pyrrolidine 5,5-trans-lactam ring system. This stereoselective functionalisation also occurs with a wide range of dif ferent electrophiles giving the analogous alpha-substituted trans-lactams. The corresponding beta-methyl pyrrolidine 5,5-trans-lactam was prepared by stereoselective methylation prior to ring closure.