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手性有机硼化合物在有机合成、医药、材料等诸多领域中有广泛的应用,发展该类化合物的高效合成方法一直广受关注.此前,我们发展了过渡金属催化卡宾对硼氢键(B—H)的插入反应,并实现了α-重氮酯对B—H键的不对称插入反应.本文以手性螺环双噁唑啉配体和铜的络合物作为催化剂,首次实现了α-重氮酮对膦-硼烷加合物的B—H键不对称插入反应,获得了较高的收率和高达83%ee的对映选择性.该研究成果是为数不多的以α-重氮酮作为卡宾前体的不对称杂原子氢键插入反应,为手性α-硼取代酮化合物这类新的有机硼化合物的合成提供了有效方法.
Chiral organoboron compounds have been widely used in organic synthesis, medicine, materials and many other fields, and the development of efficient synthesis methods for these compounds has drawn much attention. Previously, we developed the transition metal- H), and the asymmetric insertion of α-diazo ester to B-H bond has been achieved.In this paper, a chiral spiro double oxazoline ligand and copper complex were used as catalysts to achieve the first time that α - Azodinone asymmetrically inserted into the B-H bond of the phosphine-borane adduct, yielding higher yields and enantioselectivities of up to 83% ee. The results of this study are few with α - diazotone as an asymmetric hydrogen atom insertion reaction of a carbene precursor provides an effective method for the synthesis of novel organoboron compounds such as chiral α-boron substituted ketones.