Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 13, Pages 3679-3692Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003542
Keywords
carbanions; cooperative catalysis; heterocycles; ring strain; zwitterions
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Funding
- Swiss National Science Foundation (SNF)
- F. Hoffmann-La Roche
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The first catalytic asymmetric synthesis of beta-sultones is reported. This development has enabled a rapid access to a number of highly enantioenriched biologically interesting sulfonyl and sulfinyl compound classes, which makes use of the inherent ring strain of the four-membered heterocycles. The products possess either two vicinal stereocenters, such as in beta-hydroxy-sulfonamides, -sulfonates, -sulfones, -sulfonic acids, -sulfinic acids, gamma-sultines, and gamma-sultones or a single stereocenter, such as in alpha-branched alkyl or allyl sulfonic acids. This work also represents the first application of sulfene intermediates in asymmetric catalysis. The reactivity of a sulfene normally acting as an electrophile could be reverted by the formation of a nucleophilic zwitterionic sulfene-amine adduct. To achieve a combination of high enantioselectivity and reactivity, cooperative catalytic action of a chiral nucleophilic tertiary amine (the cinchona alkaloid derivative diydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)(2)PYR)) and Bi(OTf)(3) or In(OTf)(3) was of primary importance.
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