Estimating the stereoinductive potential of cinchona alkaloids with a prochiral probe approach.
Cinchona alkaloids occupy a privileged status due to their optimal possession of two desirable properties, namely catalytic efficiency and stereoselectivity. This paper proposes a new quantitative measure, the energy difference between the adducts formed by re and si face attack to Mosher's cation (DeltaMOSCA(re-si)) as a measure of stereoinductive potential, by taking the example of cinchona alkaloids. Other descriptors such as methyl cation affinities and the one based on continuous symmetry measures are also estimated and correlated with DeltaMOSCA(re-si) values.
Wei
Yin
Y
Department of Chemistry and Biochemistry, LMU München, Butenandtstrasse 5-13, D-81377 München, Germany.
Sastry
G Narahari
GN
Zipse
Hendrik
H