Michael addition-elimination reactions of chiral enolates with ethyl 3-halopropenoates.
Key dienoic or dienal substructures of cytotoxic macrolides amphidinolide E and dictyostatin have been prepared via a Michael addition (followed by elimination of X-) of chiral enolates on beta-halo derivatives of ethyl acrylate, with full retention of the initial E or Z configuration. Evans oxazolidin-2-ones and our related thiazolidin-2-ones, as well as a fine-tuning of the reaction conditions, have been essential. Many chiral building blocks are accessible from these adducts.
Esteban
Jorge
J
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Av. Diagonal 647, 08028 Barcelona, Catalonia, Spain.
Costa
Anna M
AM
Gómez
Alex
A
Vilarrasa
Jaume
J
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011407:Propane / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism; D000097442:Amphidinolides
D019086:Bridged Bicyclo Compounds, Heterocyclic; D018942:Macrolides; D011407:Propane; C452448:amphidinolide E; D000097442:Amphidinolides; C470814:dictyostatin