N,N-Dimethylaminobenzoates enable highly enantioselective Sharpless dihydroxylations of 1,1-disubstituted alkenes.
A design scenario aimed at exploring beneficial catalyst-substrate π-π stacking electronic interactions in the classical Sharpless asymmetric dihydroxylations (SAD) leads to the identification of highly polarizable allylic N,N-dimethylaminobenzoate as a remarkably efficient auxiliary for inducing high levels of enantioselectivities (up to 99% ee) in the traditionally challenging substrate class of 1,1-disubstituted aliphatic alkenes.
Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen University Town, Shenzhen, China 518055. dzw@szpku.edu.cn.
Yaohong
Y
Zhao
Xiangyou
X
Xing
Shaolong
S
Zhang
David Zhigang
DZ
Wang
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D013237:Stereoisomerism; D004124:p-Dimethylaminoazobenzene / Q000737:chemistry*
D000475:Alkenes; D004124:p-Dimethylaminoazobenzene