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Marino JP, Viso A, Lee JD, et al. Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1). J Org Chem. 1997;62(3):645-653doi: 10.1021/jo961292i.
Marino, J. P., Viso, A., Lee, J. D., Fernández De La Pradilla, R., Fernández, P., & Rubio, M. B. (1997). Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1). The Journal of organic chemistry, 62(3), 645-653. https://doi.org/10.1021/jo961292i
Marino, Joseph P., et al. "Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1)." The Journal of organic chemistry vol. 62,3 (1997): 645-653. doi: https://doi.org/10.1021/jo961292i
Marino JP, Viso A, Lee JD, Fernández De La Pradilla R, Fernández P, Rubio MB. Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1). J Org Chem. 1997 Feb 07;62(3):645-653. doi: 10.1021/jo961292i. PMID: 11671459.
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J Org Chem. 1997 Feb 07;62(3):645-653. doi: 10.1021/jo961292i.

Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1).

The Journal of organic chemistry

Joseph P. Marino, Alma Viso, Jae-Don Lee, Roberto Fernández De La Pradilla, Paloma Fernández, M. Belén Rubio

Affiliations

  1. Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain.

PMID: 11671459 DOI: 10.1021/jo961292i

Abstract

The copper-mediated S(N)2' displacement of enantiomerically pure allylic mesyloxy vinyl sulfoxides takes place with high yields and stereoselectivities. In these adducts, the newly created chiral center is adjacent to a vinyl sulfoxide functionality which should allow for subsequent chirality transfer operations. Alternatively, enantiopure alkenyl sulfones and alkenes bearing an allylic stereocenter are readily available from these adducts with high geometric control. The S(N)2' displacements of structurally related mesyloxy sulfides and sulfones with organocuprates have been examined. From a single enantiomer at the allylic alcohol position, the absolute configuration of the new chiral center may be controlled by adjusting the oxidation level on sulfur.

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