Remarkable long range effects on the diastereoface selectivity in an aldol condensation Journal Article
| Authors: | Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K. A.; Danishefsky, S. J. |
| Article Title: | Remarkable long range effects on the diastereoface selectivity in an aldol condensation |
| 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. |
| Keywords: | unclassified drug; nonhuman; polymerization; molecular interaction; conformation; reaction analysis; synthesis; genetic linkage; stereochemistry; epothilone b; chirality; 12,13 desoxyepothilone b; article; aldol; anti-cram |
| Journal Title: | Tetrahedron Letters |
| Volume: | 40 |
| Issue: | 12 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 1999-03-19 |
| Start Page: | 2267 |
| End Page: | 2270 |
| Language: | English |
| DOI: | 10.1016/s0040-4039(99)00222-1 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 16 August 2016 -- Source: Scopus |
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