[2,3] Sigmatropic Rearrangement of Ethyl 2-(Diethoxyphosphoryloxy) Allyl Sulfoxides and Selenoxides. Synthetic Applications

We have previously described regio- and stereospecific synthesis of ally1 selenides I and ally1 sulfides 2 [1]. We now report on the application of 1 and 2 as attractive precursors of new, functionalized: allylic alcohols 3, α-hydroxy ketones 4 and I, 3-dienes 5. 1 and 2 are transformed by oxidation...

Full description

Saved in:
Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1999-01, Vol.147 (1), p.385-385
Main Authors: Skowrońska, Aleksandra, Koprowski, Marek, McPartlin, Mary, Choi, Nick
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We have previously described regio- and stereospecific synthesis of ally1 selenides I and ally1 sulfides 2 [1]. We now report on the application of 1 and 2 as attractive precursors of new, functionalized: allylic alcohols 3, α-hydroxy ketones 4 and I, 3-dienes 5. 1 and 2 are transformed by oxidation into corresponding ally1 selenoxide and sulfoxide, which display stereospecific [2,3] sigmatropic rearrangement providing after hydrolysis the allylic alcohols 3. Trans configuration of 3 was established by X-ray analysis. In some cases the rearrangement is accompanied by elimination giving the 1,3-dienes 5. Compounds 3 and 5 can be easily separated by column chromatography Dephosphorylation of 3 afforded the α-hydroxy ketones 4.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509908053672