Easy transformations of vinyl N,N-diisopropyl carbamates into silyl enol ethers or aldehydes by addition of methyllithium

Homoaldols and 4-hydroxy silyl enol ethers have been prepared upon addition of methyllithium to 4-hydroxyvinyl N,N-diisopropyl carbamates obtained from Hoppe's homoaldolisation reaction followed by addition, in presence of an excess of HMPA, of water or tert-butyldimethylsilyl chloride, respect...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1999-11, Vol.40 (46), p.8103-8107
Main Authors: Madec, David, Henryon, Vivien, Férézou, Jean-Pierre
Format: Article
Language:English
Subjects:
aldehydes
carbamates
enol ethers
lithium
lithium compounds
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Homoaldols and 4-hydroxy silyl enol ethers have been prepared upon addition of methyllithium to 4-hydroxyvinyl N,N-diisopropyl carbamates obtained from Hoppe's homoaldolisation reaction followed by addition, in presence of an excess of HMPA, of water or tert-butyldimethylsilyl chloride, respectively. In the case of silyl enol ethers, a total retention of the Z configuration of the double bond was observed. This simple procedure allows an easy preparation of γ-lactones from the homoaldol adducts. Addition of methyllithium on vinyl N,N-diisopropyl carbamates led to the corresponding lithium enolates with retention of the configuration of the Z-enol function
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01699-8