Synthesis of enantiopure, densely functionalized carbocycles from vinyl nitro-modified carbohydrates

Department of Chemistry, Indian Instituteof Technology Kharagpur, Kharagpur-721 302, West Bengal, India E-mail: tpathak@chem.iitkgp.ac.in Manuscript received online 27 December 2019, revised and accepted 09 January 2020 A powerful, flexible, and stereoselective general strategy for the construction of chirally pure six-membered carbocycles from easily available vinyl nitro-modified hexofuranosides is described. By using a Michael addition reaction followed by ring opening and ring closure, densely functionalized carbasugars decorated with multiple chiral centers are obtained in good overall yields