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Stereoselective formation of tertiary and quaternary carbon centers via inverse conjugate addition of carbonucleophiles to allenic esters |
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| Authors: | Ana Lú cia Cardoso,Manuela Ramos Silva,Francisco Palacios,Alberto A.C.C. Pais |
| Affiliation: | a Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal b Department of Physics, University of Coimbra, 3004-516 Coimbra, Portugal c Department of Organic Chemistry I, Faculty of Pharmacy, University of the Basque Country, Apartado 450, 01080 Vitoria, Spain |
| Abstract: | Stereoselective inverse conjugate addition of carbonucleophiles to allenoates bearing a chiral auxiliary in the ester moiety afforded optically active α,β-unsaturated carboxylic esters bearing a new stereocenter at the δ position. The rationalization of the observed selectivity was supported by semi-empirical molecular orbital calculations. |
| Keywords: | Allenoates Carbonucleophiles Chiral α,β-unsaturated carboxylic esters Chiral carbon centers Stereoselective inverse conjugate addition |
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