Stereoselective formation of tertiary and quaternary carbon centers via inverse conjugate addition of carbonucleophiles to allenic esters

publication · 10 years ago
by Paulo E. Abreu, Ana Lúcia Cardoso, Ana Matos Beja, Manuela Ramos Silva, Jesús M. de los Santos, Francisco Palacios, Alberto A.C.C. Pais, Teresa M. V. D. Pinho e Melo (University of Coimbra, University of the Basque Country)
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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.

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