Diastereoselectivity in the Overman rearrangement of O-cyclohexylideneethylimidates

Conformationally biased cyclohexylideneethanols were prepared and converted to trichloroacetimidates, which then were subjected to the thermal Overman rearrangement. The rearrangement of axially unshielded imidates was unselective, providing isomeric amides in equal ratio. The axial face shielding i...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 23; pp. 3885 - 3887
Main Authors Jaunzeme, Ieva, Jirgensons, Aigars, Kauss, Valerjans, Liepins, Eduards
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.06.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYTIC ASYMMETRIC REARRANGEMENT
ALCOHOL
(-)-TETRODOTOXIN
1,3 TRANSPOSITION
AMINE FUNCTIONS
D-GLUCOSE
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Summary:Conformationally biased cyclohexylideneethanols were prepared and converted to trichloroacetimidates, which then were subjected to the thermal Overman rearrangement. The rearrangement of axially unshielded imidates was unselective, providing isomeric amides in equal ratio. The axial face shielding in the 3,3,5-trimethylcyclohexylidene system resulted in highly selective nitrogen attack from the equatorial side.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.03.174