Multi-component, regio-selective aldol addition of beta-ketoesters to aldehydes: scope and applications

作者:More Vijaykumar; Di Mola Antonia; Croce Gianluca; Tedesco Consiglia; Petronzi Carmen; Peduto Antonella; De Caprariis Paolo; Filosa Rosanna; Massa Antonio*
来源:Organic and Biomolecular Chemistry, 2011, 9(24): 8483-8488.
DOI:10.1039/c1ob06229h

摘要

Simple and effective multi-component one-pot aldol addition/protection reactions of beta-ketoesters to a series of aldehydes in the presence Me3SiCl and i-Pr2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.

  • 出版日期2011