Diastereoselectivity in the Carroll rearrangement of β-keto esters of tertiary allylic alcohols

Carroll rearrangement of β-keto esters derived from tertiary allylic alcohols, for example, 7 , under basic conditions followed by decarboxylation of the resulting β-keto acids yielded the expected γ,δ-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/ Z, depending...

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Bibliographic Details
Published in:Tetrahedron letters 2004, Vol.45 (1), p.107-109
Main Authors: Jung, Michael E., Duclos, Brian A.
Format: Article
Language:English
Subjects:
[3,3]-sigmatropic rearrangement
Carroll rearrangement
electronic effects
steric effects
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Summary:Carroll rearrangement of β-keto esters derived from tertiary allylic alcohols, for example, 7 , under basic conditions followed by decarboxylation of the resulting β-keto acids yielded the expected γ,δ-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/ Z, depending on the relative steric requirements of the two groups at the allylic center. Carroll rearrangement of β-keto esters derived from tertiary allylic alcohols, for example, 7 , under basic conditions followed by decarboxylation of the resulting β-keto acids yielded the expected γ,δ-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/ Z, depending on the relative steric requirements of the two groups at the allylic center.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.10.102