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New Organic Chemistry of Sulfur Dioxide

Simple 1, 3-dienes undergo highly stereoselective hetero-Diels–Alder additions with SO2 at low temperature giving sultines. These reactions that are faster than the more exothermic cheletropic additions of SO2-producing sulfolenes. This has led to the invention of a new C–C bond-forming reaction combining electron-rich dienes and alkenes with SO2. The reaction cascade has been exploited to develop combinatorial, one-pot, four-component syntheses of polyfunctional sulfones, sulfonamides, and sulfonic esters. It also allows us to generate, in one-pot operations, enantiomerically enriched polypropionate fragments containing up to three contiguous stereogenic centers and a (E)-alkene unit. These fragments can be used directly in further C–C bond-forming reactions, such as cross-aldol condensations, thus permitting the expeditious construction of complicated natural products of biological interest (e.g., Baconipyrones, Rifamycin S, Apoptolidinone) and analogues. New ene reactions of SO2 have also been discovered ; they open new avenues to organic synthesis.

SO2 chemistry ; hetero-diels-alder ; allylic sulfinic acids ; bond-forming reaction ; mediated one-pot ; ene reaction ; cheletropic additions ; polyfunctional sulfones ; 4-component synthesis ; stereoselective-synthesis ; asymmetric-synthesis

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