Stereoselective synthesis of (3E,5E)-dien-2-ones and (2E,4E)-dienals via 2-phenylsulfonyl 1,3-dienes

DOI: 10.1016/S0040-4039(00)77694-5

Source and publish data:

Tetrahedron Letters p. 131 - 134 (1992)

Update date:2022-07-29

Topics: Stereoselective synthesis

Authors:

Baeckvall, Jan-E.

Ericsson, Anna M.

Plobeck, Niklas A.

Juntunen, Seppo K.

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Article abstract of DOI:10.1016/S0040-4039(00)77694-5

Michael addition of nitroalkanes to 2-phenylsulfonyl 1,3 dienes proceeded smoothly in the presence of DBU to give nitrosulfones (e.g. 2) in high yield. Transformation of the nitro group of the adduct to a keto function (Nef type reaction) and subsequent elimination of benzenesulfinic acid afforded conjugated dienones and dienals with high stereoselectivity.

Full text of DOI:10.1016/S0040-4039(00)77694-5

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