A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp<sub>2</sub>Zr(H)Cl
作者:Jonathan M. White、Ashok Rao Tunoori、Gunda I. Georg
DOI:10.1021/ja002149g
日期:2000.12.1
Functional group manipulations continue to play an important role in organic synthesis, and hence the development of new methods to carry out these transformations remains an important part of organic chemistry. The reduction of amides to aldehydes is one such transformation, and although several methods are available,(1) many are substrate specific,(2) the outcome of the reaction being dependent upon the nature of the nitrogen substituent. Problems with existing techniques, which generally require the use of highly reactive reagents such as aluminum and boron hydrides, include low functional group tolerance, over-reduction to amines or alcohols, or the formation of other byproducts. Herein, we report a general procedure for the conversion of tertiary amides to:aldehydes, which employs a commercially available reagent, Cp2Zr(H)Cl (Schwartz reagent(3)) and operates under mild conditions at room temperature (Scheme 1).