A diastereoselective unique route to cyclopropanes functionalized at all three ring carbon atoms from acyclic vinyl sulfone-modified carbohydrates.
In a departure from the current trend of using metal-catalyzed routes to cyclopropanation, pentosyl and hexosyl vinyl sulfone-modified carbohydrates having the terminal double bond and a suitably positioned leaving group are reacted in a stereoselective fashion with a series of nucleophiles to yield a myriad of cyclopropanes substituted at all three ring carbon atoms.
Atta
Ananta Kumar
AK
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Pathak
Tanmaya
T
D002241:Carbohydrates / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D002241:Carbohydrates; D003521:Cyclopropanes; D013450:Sulfones; C009873:divinyl sulfone; D002244:Carbon