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Synfacts 2007(9): 0955-0955  
DOI: 10.1055/s-2007-968853
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

New Family of Cyclopropane-Based Tripodal Ligands: TriCyp

Contributor(s): Mark Lautens, Frédéric Ménard
H. Schill, A. de Meijere*, D. S. Yufit
Georg-August-Universität Göttingen, Germany and University of Durham, UK
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

The primary focus of this work is the practical synthesis of various members of a tripodal ligand family. TriCyp-PPP 6 was shown to be more effective than bis(diphenylphosphino)butane (dppb) in Pd-catalyzed allylic alkylation reactions. Indeed, at very low catalyst concentration, TriCyp-PPP turnover numbers (TON) were 1.5 times higher than those of dppb. A 101° bite angle is proposed to account for the TON increase (dppb = 98°). As other Pd-catalyzed reactions suffer from low TONs, this new class may provide new opportunities for improved efficiency.