STEREOSELECTIVE METHOXYSELENENYLATION OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - A METHOD FOR THE SYNTHESIS OF 1,3-ANTI-DIOLS

Authors
KIM KS PARK HB KIM JY AHN YH JEONG IH
Citation
Ks. Kim et al., STEREOSELECTIVE METHOXYSELENENYLATION OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - A METHOD FOR THE SYNTHESIS OF 1,3-ANTI-DIOLS, Tetrahedron letters, 37(8), 1996, pp. 1249-1252
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
8
Year of publication
1996
Pages
1249 - 1252
Database
ISI
SICI code
0040-4039(1996)37:8<1249:SMOAAA>2.0.ZU;2-6
Abstract
Reaction of secondary acyclic trans-allylic alcohol derivatives with P hSeBr in the presence of 2,6-di-t-butylpyridine in MeOH proceeded in a highly regio- and stereoselective manner and the subsequent reduction and deprotection of the resultant methoxyselenides afforded mostly 1, 3-anti-diols. The methoxyselenenylation of the acetate derivative of t he same allylic alcohol, on the other hand, gave several other isomers along with the 1,3-anti-diol derivative.