Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo, Kyoto 606-8502, Japan.
J Am Chem Soc. 2013 Nov 27;135(47):17667-70. doi: 10.1021/ja407764u. Epub 2013 Nov 14.
We developed herein a new chiral Brønsted acid catalyst which is composed of two independent organic molecules, a chiral diol, and 2-boronobenzoic acid. In situ formation of a boronate ester was utilized as a key process to generate an active catalyst. This boronate ester assisted chiral carboxylic acid catalyst was successfully applied to the trans-aziridination of N-Boc and N-benzyl imines with N-phenyldiazoacetamide. This is the first catalyst to achieve high enantioselectivities using N-benzyl imines.
我们开发了一种新型的手性布朗斯台德酸催化剂，它由两个独立的有机分子、手性二醇和 2-硼苯甲酸组成。利用硼酸酯的原位形成作为关键步骤来生成活性催化剂。这种硼酸酯辅助的手性羧酸催化剂成功地应用于 N-Boc 和 N-苄基亚胺与 N-苯基亚重氮乙酰胺的反氮杂环丙烷化反应。这是第一个使用 N-苄基亚胺实现高对映选择性的催化剂。
