The isomeric purity of products from certain group-selective reactions
can be significantly amplified when reactions can occur sequentially.
The theoretical basis for a strategy that exploits reactions with mod
est enantiotopic group selectivity for asymmetric synthesis is describ
ed. The relationships between conversion, yield, and isomeric purity f
or such a process are calculated using a simple kinetic model. A simpl
e method for selecting candidate group-selective reactions from known
face-selective reactions is presented. Application of the strategy is
illustrated with the reduction of D-glucose and D-galactose derived di
aldehydes with B-isopinocampheyl-9-borabicyclo[3.3.1]nonane (Alpine-Bo
rane(R)).