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

✍ Scribed by Christina R Harris; Scott D Kuduk; Aaron Balog; Ken A Savin; Samuel J Danishefsky

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 160 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00222-1

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✦ Synopsis

The stereochemical results in an aldol reaction between the enolate 2 and various a-methyl aldehydes indicates a stabilizing through space interaction between C4-C s unsaturation and the formyl group.

This interaction leads to a reaction conformation which favors a C7-C ~ (epothilone numbering) anti-relationship in the aldol products. Included is an extensive study that identifies steric and electronic effects of various ormethyl aldehydes in the aldol diastereoselection.

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