Asymmetric Diels-Alder Reactions with Sulfines Derived from Proline
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.
Broek, Leon A. G. M. van den,Porskamp, Pascal A. T. W.,Haltiwanger, R. Curtis,Zwanenburg, Binne
p. 1691 - 1695
(2007/10/02)
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