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.
Vogel
Pierre
P
Laboratoire de glycochimie et synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland. pierre.vogel@epfl.ch
Turks
Maris
M
Bouchez
Laure
L
Marković
Dean
D
Varela-Alvarez
Adrián
A
Sordo
José Angel
JA
D000900:Anti-Bacterial Agents / Q000737:chemistry; D007536:Isomerism; D009930:Organic Chemicals / Q000737:chemistry*; D013458:Sulfur Dioxide / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D009930:Organic Chemicals; D013458:Sulfur Dioxide