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

Das, Indrajit ; Pal, Tarun K. ; Suresh, Cheravakkattu G. ; Pathak, Tanmaya (2007) 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 The Journal of Organic Chemistry, 72 (15). pp. 5523-5533. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo062373+

Related URL: http://dx.doi.org/10.1021/jo062373+

Abstract

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.

Item Type:Article
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ID Code:104126
Deposited On:17 Mar 2017 09:32
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