Journal of Organic Chemistry p. 1691 - 1695 (1984)
Update date:2022-08-02
Topics: Experimental terms Asymmetric Diels-Alder Reactions Sulfines Proline
Broek, Leon A. G. M. van den
Porskamp, Pascal A. T. W.
Haltiwanger, R. Curtis
Zwanenburg, Binne
The Synthesis of a variety of sulfines 8 derived from S-proline, utilizing the reaction of α-silyl carbanions with sulfur dioxide, is described.Reaction of the thus prepared sulfines 8 with 2,3-dimethyl-1,3-butadiene gave dihydrothiopyran S-oxides 9.During these cycloaddition reactions asymmetric inductions up to 40percent were observed.From one pure diastereomeric form of cycloadduct 9d an X-ray analysis was carried out in order to provide insight in the steric course of the cycloaddition reaction.
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