Stereoselective methoxyselenenylation of acyclic allylic alcohol derivatives: A method for the synthesis of 1,3- anti-diols

Reaction of secondary acyclic trans-allylic alcohol derivatives with PhSeBr 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...

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Bibliographic Details
Published in:Tetrahedron letters 1996-02, Vol.37 (8), p.1249-1252
Main Authors: Kim, Kwan Soo, Park, Heung Bok, Kim, Ji Young, Ahn, Yeong Hee, Jeong, In Howa
Format: Article
Language:English
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Summary:Reaction of secondary acyclic trans-allylic alcohol derivatives with PhSeBr 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 the same allylic alcohol, on the other hand, gave several other isomers along with the 1,3- anti-diol derivative. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)02408-5