STEREOSELECTIVE [2,3]-SIGMATROPIC WITTIG REARRANGEMENT OF BENZYL ETHERS DERIVED FROM VINYLCUPRATE ADDUCTS OF (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE

Allyl alcohols 2 prepared by addition of lithium vinylcuprates to (R)-2,3-O-isopropylideneglyceraldehyde (1) are converted to 3,4,5-trimethoxybenzyl ethers 3 by a one-pot desilylation/alkylation. After deprotonation using potassium t-butoxide/t-butyllithium/N,N,N',N'-tetramethylethylenedia...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 51; no. 33; pp. 9023 - 9030
Main Authors METZ, P, SCHOOP, A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 14.08.1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACYCLIC STEREOCONTROL
SIGMATROPIC REARRANGEMENTS
<2,3>-WITTIG REARRANGEMENT
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary:Allyl alcohols 2 prepared by addition of lithium vinylcuprates to (R)-2,3-O-isopropylideneglyceraldehyde (1) are converted to 3,4,5-trimethoxybenzyl ethers 3 by a one-pot desilylation/alkylation. After deprotonation using potassium t-butoxide/t-butyllithium/N,N,N',N'-tetramethylethylenediamine in t-butyl methyl ether at -78 degrees C, substrates 3 undergo a [2,3]-sigmatropic Wittig rearrangement with complete 1,3-chirality transfer and good simple diastereoselectivity to give homoallyl alcohols 5 as the major products.
ISSN:0040-4020
DOI:10.1016/0040-4020(95)00497-V