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1999•Tetrahedron LettersOpen access

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

Christina R. Harris, Scott D. Kuduk, Aaron Balog, Ken Savin, Samuel J. Danishefsky

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Abstract

The stereochemical results in an aldol reaction between the enolate 2 and various α-methyl aldehydes indicates a stabilizing through space interaction between C4C5 unsaturation and the formyl group. This interaction leads to a reaction conformation which favors a C7C8 (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.

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The stereochemical results in an aldol reaction between the enolate 2 and various α-methyl aldehydes indicates a stabilizing through space interaction between C4C5 unsaturation and the formyl group. This interaction leads to a reaction conformation which favors a C7C8 (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.

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Available abstract

The stereochemical results in an aldol reaction between the enolate 2 and various α-methyl aldehydes indicates a stabilizing through space interaction between C4C5 unsaturation and the formyl group. This interaction leads to a reaction conformation which favors a C7C8 (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.

Key concepts: Chemistry, Aldol reaction, Aldol condensation, Steric effects, Selectivity, Stereochemistry, Degree of unsaturation, Organic chemistry

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