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

被引：31
作者：
Horiguchi, Kosaku [1 ]
Yamamoto, Eri [2 ]
Saito, Kodai [1 ,3 ]
Yamanaka, Masahiro [2 ]
Akiyama, Takahiko [1 ]
机构：
[1] Gakushuin Univ, Dept Chem, Toshima Ku, 1-5-1 Mejiro, Tokyo 1718588, Japan
[2] Rikkyo Univ, Dept Chem, Toshima Ku, 3-34-1 Nishi Ikebukuro, Tokyo 1718501, Japan
[3] Keio Univ, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 24期
关键词：
dynamic kinetic resolution; heterocycles; hydrogenation; organocatalysis; stereoselective synthesis; ORGANOCATALYTIC TRANSFER HYDROGENATION; CATALYZED TRANSFER HYDROGENATION; FRIEDEL-CRAFTS REACTIONS; MANNICH-TYPE REACTION; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; REDUCTIVE AMINATION; ALIPHATIC-KETONES; MUKAIYAMA ALDOL; HANTZSCH ESTERS;
D O I：
10.1002/chem.201601611
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：8078 / 8083
页数：6
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