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.
Highlights
In this manuscript, phosphine-dependent [3 + 3] and [4 + 3] annulation reactions of allenoate with aziridines were disclosed
Aziridines are an important type of versatile building blocks for synthesis of diverse nitrogen-containing heterocyclic compounds and natural products.[12]
Prepared according to the general procedure as described above catalyzed by EtPPh2 in 69% yield (43.3 mg)
Summary
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 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. The results showed that the aprotic CH2Cl2 remained to be the best solvent, while MeOH gave excellent reaction selectivity but low yield of cycloadducts (entry 16). The annulation reaction worked well with 2-naphthyl substituted aziridine (1n), affording the corresponding product in 58% yield (entry 14). The reaction works efficiently under mild conditions to give functionalized tetrahydroazepines in moderate to excellent yield with moderate to excellent diastereoselectivity
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