American Chemical Society
jo6b02659_si_001.pdf (3.68 MB)

Phosphine-Catalyzed Enantioselective [2+4] Cycloaddition to Synthesize Pyrrolidin-2-one Fused Dihydropyrans Using α‑Substituted Allenoates as C2 Synthons

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journal contribution
posted on 2016-12-19, 00:00 authored by Chang Wang, Hao Jia, Cheng Zhang, Zhenzhen Gao, Leijie Zhou, Chunhao Yuan, Yumei Xiao, Hongchao Guo
A bifunctional phosphine-catalyzed highly enantioselective [2+4] cycloaddition of α-substituted allenoates with (E)-1-benzyl-4-olefinicpyrrolidine-2,3-diones has been achieved, giving pyrrolidin-2-one fused dihydropyran derivatives in moderate to good yields with excellent enantioselectivities (up to 98% ee). This reaction provides a useful catalytic asymmetric access to dihydropyran structural motifs.