title: Sulfinyl group as an intramolecular nucleophile: synthesis of bromohydrins from beta-methyl-gamma,delta-unsaturated sulfoxides with high 1,2-asymmetric induction.
abstract: Bromohydrins have been prepared from beta-methyl-gamma,delta-unsaturated sulfoxides with high regio- and stereoselectivity. The reaction proceeds via neighboring group participation of the sulfinyl moiety with inversion of sulfoxide configuration as proven by an (18)O labeling study and X-ray crystallography.
authors.affiliation: Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. purush101@yahoo.com
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.forename: S Ramakrishna
authors.initials: SR
authors.lastname: Reddy
authors.forename: K A
authors.initials: KA
authors.lastname: Tony
authors.forename: Ch Naveen
authors.initials: ChN
authors.lastname: Kumar
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Varma
authors.forename: Ashwini
authors.initials: A
authors.lastname: Nangia