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Synfacts 2007(8): 0828-0828  
DOI: 10.1055/s-2007-968730
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Conjugate Addition of Indoles to Enones

Contributor(s): Mark Lautens, Frédéric Ménard
H. Yang, Y.-T. Hong, S. Kim*
Korea Advanced Institute of Science and Technology, Daejeon, Korea
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

The report illustrates another example of the versatile catalytic activity of the Cu(II)(BOX) system. The Michael addition of indoles to various α,β-unsaturated ketones yielded enantioenriched β-keto phosphonates 3, which can be further derivatized. The β-keto phosphonate in 2 provides two-point binding to the copper metal center.