Development of a new carbon-carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones

At low temperature 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or Bronstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma -unsaturated silyl sulfinates can be desilylated and reacted with methyl iodide to provide polyfunctional sulfones. Exploratory studies of this four-component synthesis of sulfones are reported. Enantiomerically pure derivatives containing up to three new stereogenic centers can be obtained using enantiomerically pure (EE)-1-alkoxy-2-methylpenta-1,3-dienes derived from (alpha -methyl benzyl alcohols, including the Greene's chiral auxiliary. The stereochemistry of the reactions is consistent with a mechanism involving the suprafacial hetero-Diels-Alder addition of sulfur dioxide to the 1-alkoxy-1,3-dienes that are rapidly ionized into zwitterionic intermediates.


Published in:
Journal of Organic Chemistry, 66, 15, 5080-5093
Year:
2001
ISSN:
0022-3263
Keywords:
Note:
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland. Univ Lausanne, Inst Cristallog, BSP, CH-1015 Lausanne, Switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-01-27


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