Synfacts 2008(3): 0272-0272  
DOI: 10.1055/s-2008-1042701
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

1,2,3-Trisubstituted Indanes via Tandem Conjugate Additions

Contributor(s): Mark Lautens, Frédéric Ménard
C. Navarro, A. G. Csákӱ*
Universidad Complutense, Madrid, Spain
Further Information

Publication History

Publication Date:
21 February 2008 (online)


The method provides a simple way to prepare highly substituted indane molecules. In one domino sequence, a boronic acid added to the unsaturated system and the resulting enolate cyclizes on the pendant second Michael acceptor. The diastereoselectivity observed was good and favored the thermodynamically more stable all-trans product. Though esters were not suitable substrates for the reaction, the authors showed that they could still be accessed via a Baeyer-Villiger oxidation of the phenyl ketones.