A versatile route to (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines and their haloamidation reaction.
Alpha-chloro ynones have been reduced using Noyori's Ru catalyst to furnish alpha-chloro propargylic alcohols with excellent enantioselectivity. These have been used as a common precursor for the preparation of (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines. The latter serve as precursors for the highly regio- and stereoselective preparation of bromo carbamates.
Raghavan
Sadagopan
S
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sraghaVan@iict.res.in
Mustafa
Shaik
S
Sridhar
B
B
D000438:Alcohols / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis; D007097:Imines / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D000480:Alkynes; D002219:Carbamates; D006842:Hydrocarbons, Brominated; D007097:Imines; D007659:Ketones; D020005:Propanols; D013457:Sulfur Compounds; C028255:propargyl alcohol