Journal article
New organic chemistry of sulfur dioxide.
- Vogel P Laboratoire de glycochimie et synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland. pierre.vogel@epfl.ch
- Turks M
- Bouchez L
- Marković D
- Varela-Alvarez A
- Sordo JA
- 2007-08-10
Published in:
- Accounts of chemical research. - 2007
English
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.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1021/ar700096h
- PMID 17685582
- Persistent URL
- https://sonar.ch/global/documents/225459
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