Tetrahedron Letters p. 131 - 134 (1992)
Update date:2022-07-29
Topics: Stereoselective synthesis
Baeckvall, Jan-E.
Ericsson, Anna M.
Plobeck, Niklas A.
Juntunen, Seppo K.
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.
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