Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways

Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo

doi:10.1039/C8RA09852B

Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways†

Honglei Liu,‡^a Yan Lin,‡^a Yan Zhao,^a Miaoren Xiao,^b Leijie Zhou,^a Qijun Wang,^a Cheng Zhang,

^a Dongqi Wang,^b Ohyun Kwon

*^c and Hongchao Guo

*^a

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* Corresponding authors

^a Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
E-mail: hchguo@cau.edu.cn

^b Institute of High Energy Physics, Chinese Academy of Science, 19B Yuquan Lu, Shijingshan District, Beijing 100049, P. R. China

^c Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA
E-mail: ohyun@chem.ucla.edu

Abstract

In this manuscript, phosphine-dependent [3 + 3] and [4 + 3] annulation reactions of allenoate with aziridines were disclosed. The alkyldiphenylphosphine-promoted [4 + 3] annulation of allenoate with aziridines has been achieved under mild conditions, providing biologically interesting functionalized tetrahydroazepines in moderate to excellent yield with moderate to excellent regioselectivity and diastereoselectivity.

RSC Advances

Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways†

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Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways

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