Stereoselective [2,3]-sigmatropic wittig rearrangement of benzyl ethers derived from vinylcuprate adducts of ( R)-2,3- O-isopropylidenegiyceraldehyde
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...
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| Published in | Tetrahedron Vol. 51; no. 33; pp. 9023 - 9030 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Ltd
14.08.1995
|
| Online Access | Get full text |
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| 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 °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 1464-5416 |
| DOI: | 10.1016/0040-4020(95)00497-V |