Chiral Organocatalyzed Intermolecular Rauhut–Currier Reaction of Nitroalkenes with Ethyl Allenoate

Shinobu Takizawa; Makoto Sako; Kenta Kishi; Masashi Shigenobu; Giang Vo-Thanh; Hiroaki Sasai

doi:10.1248/cpb.c17-00554

Communications to the Editor

Chiral Organocatalyzed Intermolecular Rauhut–Currier Reaction of Nitroalkenes with Ethyl Allenoate

Shinobu Takizawa , Makoto Sako, Kenta Kishi, Masashi Shigenobu, Giang Vo-Thanh, Hiroaki Sasai

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Keywords: Rauhut–Currier reaction, chiral organocatalysis, nitroalkene, α-functionalized allenoate

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Supplementary material

2017 Volume 65 Issue 11 Pages 997-999

DOI https://doi.org/10.1248/cpb.c17-00554

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Abstract

An enantioselective intermolecular Rauhut–Currier (RC) reaction of nitroalkenes with ethyl allenoate has been established with quinidine-derived β-isocupreidine. The present RC reaction afforded α-functionalized allenoates 3 in up to 94% yield with 59% enantiomeric excess (ee).

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