Synfacts 2008(3): 0285-0285  
DOI: 10.1055/s-2008-1042695
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Aldol Synthesis via Radical Addition to Cyclic Enones

Contributor(s): Mark Lautens, Valentina Aureggi
M. P. Sibi*, S. Nad
North Dakota State University, Fargo, USA
Further Information

Publication History

Publication Date:
21 February 2008 (online)


The development of a chiral Lewis acid mediated radical conjugate addition to cyclic enones is reported. This versatile method provides cyclic anti-aldol products of various ring sizes in high yields and excellent diastereo- and enantio­selectivities. It constitutes not only a new example (among the rare enantioselective radical addition reactions), but also an efficient alternative to the classical aldol synthetic methods via anionic intermediates, especially for the difficult coupling of bulky aldehyde counterparts with cyclic ketones.