Catalytic Asymmetric Direct Henry Reaction of Ynals: Short Syntheses of (2S,3R)-(+)-Xestoaminol C and (−)-Codonopsinines

Authors

  • Dr. Daisuke Uraguchi,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603 (Japan), Fax: (+81) 52-789-3338
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  • Shinji Nakamura,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603 (Japan), Fax: (+81) 52-789-3338
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  • Prof. Dr. Takashi Ooi

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603 (Japan), Fax: (+81) 52-789-3338
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  • This work was supported by grants from the JSPS for Scientific Research, the Global COE program in Chemistry of Nagoya University, and the Asahi Glass Foundation.

Abstract

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Triple for all: Various optically active anti-β-nitro propargylic alcohols are synthesized by the catalytic stereoselective addition of nitroalkanes to ynals (the direct Henry reaction of ynals). The utilization of the rich chemistry of carbon–carbon triple bond allows rapid access to three natural products.

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