ASYMMETRIC DIHYDROXYLATION (AD) CYCLIZATION OF N-DIBOC ALLYLIC AND HOMOALLYLIC AMINES - SELECTIVE DIFFERENTIATION OF THE HYDROXYL-GROUPS/

Authors
WALSH PJ BENNANI YL SHARPLESS KB
Citation
Pj. Walsh et al., ASYMMETRIC DIHYDROXYLATION (AD) CYCLIZATION OF N-DIBOC ALLYLIC AND HOMOALLYLIC AMINES - SELECTIVE DIFFERENTIATION OF THE HYDROXYL-GROUPS/, Tetrahedron letters, 34(35), 1993, pp. 5545-5548
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
35
Year of publication
1993
Pages
5545 - 5548
Database
ISI
SICI code
0040-4039(1993)34:35<5545:AD(CON>2.0.ZU;2-Y
Abstract
Asymmetric dihydroxylation of N-diBoc protected allylic and homoallyli c amines with in situ cyclization affords the corresponding oxazolidin ones in good yields. The enantioselectivity is dependent on the substi tution pattern of the olefin and ranges from 34 - 98%. This methodolog y allows selective differentiation of the hydroxyl groups formed in th e AD and increases the potential applications of the resulting product s.