Asymmetric synthesis of cyclic beta-amino acids

Authors
O'Brien, P Porter, DW Smith, NM
Citation
P. O'Brien et al., Asymmetric synthesis of cyclic beta-amino acids, SYNLETT, (9), 2000, pp. 1336-1338
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
2000
Pages
1336 - 1338
Database
ISI
SICI code
0936-5214(200009):9<1336:ASOCBA>2.0.ZU;2-G
Abstract
A convenient synthesis of cyclic beta -amino acid derivatives (5-, 6- and 7 -rings) is achieved via a four step sequence: (i) stereoselective Michael a ddition of substituted alpha -methylbenzylamines to alpha,beta -unsaturated chloroesters; (ii) CAN-mediated deprotection; (iii) cyclisation and (iv) a lpha -chloroethyl chloroformate-mediated amethylbenzylamine deprotection.