Sarotti Ariel M, Pellegrinet Silvina C
Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario (2000), Argentina.
J Org Chem. 2009 May 1;74(9):3562-5. doi: 10.1021/jo900346u.
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.
手性β-烯丙基-10-取代-9-硼双环[3.3.2]癸烷是醛和酮对映选择性烯丙基硼化反应的高效试剂。在本研究中，我们使用密度泛函理论（DFT）计算来解释实验观察到的反应活性和选择性。计算结果正确地再现了实验反应活性趋势和对映选择性。我们的结果表明，面选择性的起源强烈依赖于空间效应。
