Synfacts 2005(1): 0124-0124  
DOI: 10.1055/s-2005-872193
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioenriched α,β-Unsaturated Lactones via Vinylogous Mukaiyama Aldol

Contributor(s): Mark Lautens, Andrew Martins
X. Moreau, B. Bazán-Tejeda, J.-M. Campagne*
ICSN-CNRS, Gif-sur-Yvette, France
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Publication History

Publication Date:
21 September 2005 (online)


From easily accessible starting materials, a variety of enantioenriched α,β-unsaturated six-membered lactones can be synthesized. This method demonstrates a facile route towards a challenging target. Even ketones with similar flanking substituents led to products with high ee. Neither electron-rich nor electron-poor aromatic ketones were well tolerated; and α,β-unsaturated ketones also gave poor results.