Origin of 1,3-induction in the addition of alkyl lithium to imines bearing an N-stereogenic center.
The origin of diastereoselectivity in the addition of alkyl lithium to chiral Schiff bases has been investigated experimentally and theoretically and the formation of the major diastereomer can be explained from the energy minimized structure of the Schiff base in which the phenyl group has been found to orient in such a manner that it posed lesser steric hindrance to the incoming nucleophile as compared to the alkyl group.
Nancy
Department of Chemistry, Panjab University, Chandigarh-160 014, India.
Ghosh
Soma
S
Singh
Nishan
N
Kaur Nanda
Gurmeet
G
Venugopalan
P
P
Bharatam
Prasad V
PV
Trehan
Sanjay
S