American Chemical Society
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Diastereoselective C−C Bond Formation at C-5 of Vinyl Sulfone-Modified Hex-5-enofuranosyl Carbohydrates:  Diversity-Oriented Synthesis of Branched-Chain Sugars and Beyond

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posted on 2020-04-02, 13:42 authored by Indrajit Das, Tarun K. Pal, Cheravakkattu G. Suresh, Tanmaya Pathak
This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-5-enofuranosides. The stereoelectronic properties of the substituents at the C-3 position and their interactions with the incoming carbon nucleophiles control the diastereoselectivity of addition at the C-5 position, favoring the formation of l-ido derivatives as major products in most of the cases studied. This new concept of stereocontrolled carbon−carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature. The novel chirons generated by this diversity-oriented synthetic method have been implemented in the preparation of a wide range of hexofuranosyl C-5 branched-chain sugars, bicyclic derivatives, chirally pure enals, and densely functionalized carbocycles.