Asymmetric Vicinal Acylation of Olefins - a New Approach To Enantiomerically Pure Gamma-lactones

Génicot, Christophe;Ghosez, Léon
(1992) Tetrahedron Letters — Vol. 33, n° 48, p. 7357-7360 (1992)

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Abstract
Amide 3 derived from N-tosylsarcosine and (2R,5R)-dimethylpyrrolidine was converted into keteniminium salt 4 which readily cycloadded to olefins. Hydrolysis of the adducts yielded cyclobutanones which were regiospecifically oxidized to gamma-lactones 7. High enantioselectivities were observed with 1,2-cis-disubstitued olefins.
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Génicot, C., & Ghosez, L. (1992). Asymmetric Vicinal Acylation of Olefins - a New Approach To Enantiomerically Pure Gamma-lactones. Tetrahedron Letters, 33(48), 7357-7360. https://doi.org/10.1016/S0040-4039(00)60187-9 (Original work published 1992)