Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Org Lett. 2020 Mar 20;22(6):2225-2229. doi: 10.1021/acs.orglett.0c00430. Epub 2020 Feb 27.
The chiral indole is an important structure in organic chemistry. We have developed an enantioselective hydrogen transfer reaction of indolylmethanol, which is characterized by the combined use of benzothiazoline and a newly synthesized chiral phosphoric acid. The reaction furnished indoles bearing a chiral tertiary carbon center at the 3-position in high to excellent yields and with excellent enantioselectivities, most of which are greater than 95% ee. The chiral indole was converted into an inhibitor of leukotriene production while retaining excellent ee.
手性吲哚是有机化学中的重要结构。我们开发了一种吲哚甲醇的对映选择性氢转移反应，其特点是联合使用苯并噻唑啉和一种新合成的手性磷酸。该反应以高至优异的收率和优异的对映选择性提供了在 3 位带有手性叔碳中心的吲哚，其中大多数大于 95%ee。手性吲哚转化为白三烯产生的抑制剂，同时保持优异的 ee。
