| Abstract
| - This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modifiedhex-5-enofuranosides. The stereoelectronic properties of the substituents at the C-3 position and theirinteractions with the incoming carbon nucleophiles control the diastereoselectivity of addition at the C-5position, favoring the formation of l-ido derivatives as major products in most of the cases studied. Thisnew concept of stereocontrolled carbon−carbon bond formation in vinyl sulfone-modified carbohydratesis general in nature. The novel chirons generated by this diversity-oriented synthetic method have beenimplemented in the preparation of a wide range of hexofuranosyl C-5 branched-chain sugars, bicyclicderivatives, chirally pure enals, and densely functionalized carbocycles.
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