Chiral Zirconium-Catalyzed Asymmetric Mannich-Type Reactions Using Acylhydrazones as Imine Equivalents

• Shu Kobayashi

  Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST)

• Yoshiki Hasegawa

  Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST)

• Haruro Ishitani

  Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST)

抄録

In the presence of a catalytic amount of a new zirconium catalyst, prepared from zirconium(IV) t-butoxide and (R)-3,3′-dibromo-1,1′-bi-2-naphthol, 4-trifluoromethylbenzoylhydrazones reacted with silyl enolates to afford the corresponding adducts, β-N′-acylhydrazinocarbonyl compounds, in good yields with high enantiomeric excesses. Reductive cleavage of the nitrogen-nitrogen bond of the hydrazino compound using samarium diiodide gave a chiral β-aminocarbonyl compound. In addition, the hydrazino compound was also successfully converted to chiral β-lactam and pyrazolidinone derivatives.

収録刊行物

• Chemistry Letters

  Chemistry Letters 27 (11), 1131-1132, 1998-11-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360846644039576704
• NII論文ID: 10004700924
• NII書誌ID: AA00603318
• DOI: 10.1246/cl.1998.1131
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/27/11/1131/56073355/cl.1998.1131.pdf
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