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.
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.
Das
Indrajit
I
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Pal
Tarun K
TK
Suresh
Cheravakkattu G
CG
Pathak
Tanmaya
T
D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D002241:Carbohydrates; D013450:Sulfones; C009873:divinyl sulfone; D002244:Carbon