stereospecific cross-coupling reaction oriented toward efficient synthesis of non-naturally occurring amino acids

2014 Fiscal Year Final Research Report

• Project/Area Number: 25810061
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: TAKEDA Youhei 大阪大学, 工学(系)研究科(研究院), 助教 (60608785)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: アジリジン / クロスカップリング / アミノ酸 / パラジウム / ボリル化 / 位置選択的反応 / 立体特異的反応 / ボロン酸

Outline of Final Research Achievements

A regioselective and enantiospecific cross-coupling reaction of N-tosyl-2-arylaziridines with arylboronic acids to give enantiopure 2-aryl-beta-phenethylamine derivatives in high yields has been realized under the effect of a catalytic amount of Pd complex bearing a NHC ligand. Under the similar reaction conditions, 2-carboxy ester-substituted aziridines underwent a regioselective cross-coupling to give non-naturally occurring beta-amino acid derivatives in moderate yields. Furthermore, a Pd-catalyzed regioselective ring-opening borylation of 2-arylaziridines has been found.

Free Research Field

有機合成化学、有機機能化学、有機金属化学