Asymmetric Allylboration Reactions with Soderquist’s Chiral 10-Substituted-9-borabicyclo[3.3.2]decanes: A Theoretical Study

Chiral B-allyl-10-substituted-9-borabicyclo[3.3.2]decanes are highly efficient reagents for the enantioselective allylboration of adehydes and ketones. In this study, we use DFT calculations to rationalize the experimentally observed reactivity and selectivity. Calculations correctly reproduced the experimental reactivity trends and enantioselectivities. Our results suggest that the origin of the facial selectivity relies strongly on steric effects.