Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid

作者：Horiguchi Kosaku; Yamamoto Eri; Saito Kodai; Yamanaka Masahiro; Akiyama Takahiko

来源：Chemistry - A European Journal, 2016, 22(24): 8078-8083.

DOI：10.1002/chem.201601611

• dynamic kinetic resolution
• heterocycles
• hydrogenation
• organocatalysis
• stereoselective synthesis

Asymmetric synthesis of tetrahydrobenzodiazepines was achieved by transfer hydrogenation of dihydrobenzodiazepines with benzothiazoline having a hydrogenbonding donor substituent by means of a newly synthesized chiral phosphoric acid. This method was applicable to various racemic dihydrobenzodiazepines to give the corresponding products in good yields with excellent diastereoselectivities and enantioselectivities taking advantage of the dynamic kinetic resolution. Furthermore, the effect of bulky substituent at 3,3'-position on the catalyst and hydrogen-bonding donor substituent on benzothiazoline was fully elucidated by the theoretical study.

• 出版日期2016-6-6