Cinchona alkaloid/sulfinyl chloride combinations: enantioselective sulfinylating agents of alcohols.
We report a novel approach to asymmetric sulfinylation reactions based on a cinchona alkaloid/sulfinyl chloride combination that acts as the first asymmetric sulfinylating agents of achiral alcohols. Both enantiomers of arenesulfinates are obtained with up to 99% ee. The significantly high enantioselectivity observed in this case could be explained by dynamic kinetic resolution.
Shibata
Norio
N
Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan. nozshiba@nitech.ac.jp
Matsunaga
Mitsuharu
M
Nakagawa
Masaya
M
Fukuzumi
Takeo
T
Nakamura
Shuichi
S
Toru
Takeshi
T
D000438:Alcohols / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D002930:Cinchona Alkaloids; D013441:Sulfinic Acids