A NEW SYNTHESIS OF ALPHA-METHYLSERINE BY NUCLEOPHILIC RING-OPENING OFN-SULFONYL AZIRIDINES

Authors
WIPF P VENKATRAMAN S MILLER CP
Citation
P. Wipf et al., A NEW SYNTHESIS OF ALPHA-METHYLSERINE BY NUCLEOPHILIC RING-OPENING OFN-SULFONYL AZIRIDINES, Tetrahedron letters, 36(21), 1995, pp. 3639-3642
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
21
Year of publication
1995
Pages
3639 - 3642
Database
ISI
SICI code
0040-4039(1995)36:21<3639:ANSOAB>2.0.ZU;2-Z
Abstract
Conversion of tritylated 2-methylglycidol to the corresponding aziridi ne occurs by Staudinger cyclization of the intermediate azido alcohol. After N-sulfonylation with Ses-Cl and ring-opening with benzyl alcoho l, oxidation of the primary alcohol provides N,O-bisprotected alpha-me thylserine directly suitable for repetitive peptide synthesis. This se quence represents a general enantioselective protocol for the synthesi s of alpha-methylserine and other alpha,alpha-disubstituted amino acid s.