Sulfinyl group as an intramolecular nucleophile: synthesis of bromohydrins from beta-methyl-gamma,delta-unsaturated sulfoxides with high 1,2-asymmetric induction.
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.
Raghavan
Sadagopan
S
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. purush101@yahoo.com
Reddy
S Ramakrishna
SR
Tony
K A
KA
Kumar
Ch Naveen
ChN
Varma
Ashok K
AK
Nangia
Ashwini
A