2,2-DIFLUORO-1,3,2-OXAZABOROLIDIN-5-ONES - NOVEL-APPROACH FOR SELECTIVE SIDE-CHAIN PROTECTION OF SERINE AND THREONINE

Authors
WANG JD OKADA Y LI W YOKOI T ZHU JT
Citation
Jd. Wang et al., 2,2-DIFLUORO-1,3,2-OXAZABOROLIDIN-5-ONES - NOVEL-APPROACH FOR SELECTIVE SIDE-CHAIN PROTECTION OF SERINE AND THREONINE, Journal of the Chemical Society. Perkin transactions. I, (5), 1997, pp. 621-624
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
5
Year of publication
1997
Pages
621 - 624
Database
ISI
SICI code
0300-922X(1997):5<621:2-NFS>2.0.ZU;2-I
Abstract
2,2-Difluoro-1,3,2-oxazaborolidin-5-ones 1, which are synthesized from BF3 and salts of amino acids, are highly effective, convenient and, m oreover, inexpensive intermediates for the simultaneous protection of both alpha-amino and alpha-carboxy groups in alpha-amino acids. The ne w method streamlines the hitherto tedious procedures for side-chain pr otection of Ser and Thr. Ser(Bu(t)), Thr(Bu(t)), Ser(Bzl) and Thr(Bzl) are obtained by this procedure in high yields and in pure form using highly reactive reagents.