Remarkable long range effects on the diastereoface selectivity in an aldol condensation

The stereochemical results in an aldol reaction between the enolate 2 and various α-methyl aldehydes indicates a stabilizing through space interaction between C 4C 5 unsaturation and the formyl group. This interaction leads to a reaction conformation which favors a C 7C 8 (epothilone numbering) an...

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Bibliographic Details
Published in:Tetrahedron letters 1999-03, Vol.40 (12), p.2267-2270
Main Authors: Harris, Christina R, Kuduk, Scott D, Balog, Aaron, Savin, Ken A, Danishefsky, Samuel J
Format: Article
Language:English
Subjects:
aldol
anti-Cram
Epothilone B
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Summary:The stereochemical results in an aldol reaction between the enolate 2 and various α-methyl aldehydes indicates a stabilizing through space interaction between C 4C 5 unsaturation and the formyl group. This interaction leads to a reaction conformation which favors a C 7C 8 (epothilone numbering) anti-relationship in the aldol products. Included is an extensive study that identifies steric and electronic effects of various α-methyl aldehydes in the aldol diastereoselection. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00222-1