Asymmetric Aldol/Vinylogous Aldol/Cyclization Reaction Using Phosphine Oxide Catalysts

Nathan Ray Alim; Shiki Miyazaki; Yasushi Shimoda; Masaharu Sugiura; Makoto Nakajima; Shunsuke Kotani

doi:10.1248/cpb.c17-00540

Notes

Asymmetric Aldol/Vinylogous Aldol/Cyclization Reaction Using Phosphine Oxide Catalysts

Nathan Ray Alim, Shiki Miyazaki, Yasushi Shimoda, Masaharu Sugiura, Makoto Nakajima, Shunsuke Kotani

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Keywords: phosphine oxide, pyranone, asymmetric catalysis, tandem reaction, remote-control

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2017 Volume 65 Issue 10 Pages 989-993

DOI https://doi.org/10.1248/cpb.c17-00540

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Abstract

Chiral phosphine oxide sequentially activates silicon tetrachloride and trichlorosilyl enol ethers to facilitate asymmetric aldol/vinylogous aldol reaction of 4-methoxy-3-penten-2-one and conjugated aldehydes in a highly enantioselective fashion, and the subsequent cyclization produced optically active 2,6-disubstituted 2,3-dihydro-4-pyranones bearing stereogenic centers at a remote position in a single operation.

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