PAPER	Synthesis 2005: 57-60   DOI: 10.1055/s-2004-834909
© Georg Thieme Verlag Stuttgart · New York
CeCl3·7H2O/NaI-Promoted Stereoselective Aldol Coupling of α,β-Acetylenic Ketones
Jhillu S. Yadav*, B. V. S. Reddy, Manoj Kumar Gupta, B. Eeshwaraiah
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Received 9 June 2004

Abstract

A simple and highly stereoselective method has been developed for the synthesis of (Z)-β-iodo Baylis-Hillman adducts using CeCl₃·7H₂O/NaI as an inexpensive and readily available reagent system. High conversions and enhanced Z-selectivity together with the environmentally benign nature of the CeCl₃/NaI reagent system makes this method an attractive alternative to established methods.

Key words

cerium compounds - three component reaction - β-iodovinyl ketones