Direct Asymmetric Vinylogous Mannich Addition of 3,5-Disubstituted-4-nitroisoxazoles to Isatin-Derived Imines Catalyzed by a Bifunctional Phase-Transfer-Catalyst

作者：Xia, Xuejian; Zhu, Qiongqiong; Wang, Jing; Chen, Jie; Cao, Weiguo; Zhu, Bo^*; Wu, Xiaoyu^*

来源：Journal of Organic Chemistry, 2018, 83(23): 14617-14625.

DOI：10.1021/acs.joc.8b02439

• ENANTIOSELECTIVE SYNTHESIS
• CONJUGATE ADDITION
• MICHAEL ADDITION
• HIGHLY EFFICIENT
• KETIMINES
• 4-NITROISOXAZOLES
• PROLIFERATION
• DERIVATIVES
• ANTAGONIST
• DISCOVERY

Asymmetric Mannich-type addition of 3,5-disubstituted-4-nitroisoxazoles to isatin-derived Boc-protected imines has been realized by using 0.01 equiv of amide phosphonium salt as a phase transfer catalyst. Our current methodology allows for the formation of 3-isoxazolylmethyl-substituted 3-aminooxindoles in excellent yields with good to excellent enantioselectivities. The practical value of this methodology was exemplified by a gram-scale synthesis of 5an, a key intermediate for the formal synthesis (+)-AG-041R.

• 出版日期2018-12-7
• 单位河南师范大学; 上海大学