A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp₂Zr(H)Cl

Jonathan M. White, Ashok Rao Tunoori and Gunda I. Georg

*Department of Medicinal Chemistry University of Kansas Lawrence, Kansas 66045, Email: georgumn.edu

J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc., 2000, 122, 11995-11996.

DOI: 10.1021/ja002149g

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Abstract

The reduction of tertiary amides to aldehydes via Cp₂Zr(H)Cl shows several distinct advantages: The reaction requires a very short reaction time and provides very high yields of the aldehydes with good chemoselectivity. Furthermore, the reaction does not require extensive workup procedures, nor does it require scrupulously dry conditions. Additionally, substrate dependence is minimal.

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proposed mechanism

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Key Words

reduction of amides, Schwartz reagent

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ID: J48-Y2000