ASYMMETRIC DIHYDROXYLATION OF OLEFINS CONTAINING SULFUR - CHEMOSELECTIVE OXIDATION OF C-C DOUBLE-BONDS IN THE PRESENCE OF SULFIDES, 1,3-DITHIANES, AND DISULFIDES

Authors
WALSH PJ HO PT KING SB SHARPLESS KB
Citation
Pj. Walsh et al., ASYMMETRIC DIHYDROXYLATION OF OLEFINS CONTAINING SULFUR - CHEMOSELECTIVE OXIDATION OF C-C DOUBLE-BONDS IN THE PRESENCE OF SULFIDES, 1,3-DITHIANES, AND DISULFIDES, Tetrahedron letters, 35(29), 1994, pp. 5129-5132
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
29
Year of publication
1994
Pages
5129 - 5132
Database
ISI
SICI code
0040-4039(1994)35:29<5129:ADOOCS>2.0.ZU;2-Z
Abstract
Osmium tetroxide catalyzed oxidation of sulfide containing olefins in the presence of the chiral ligands (DHQD)(2)PHAL and (DHQ)(2)PHAL resu lted in the chemoselective oxidation of the C-C double bond rather tha n oxidation at sulfur. The enantioselectivity is dependent on the subs titution pattern of the olefin and ranges from 61-98%. The AD can be p erformed in the presence of the disulfide and 1,3-dithiane functional groups, also.