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Synfacts 2007(7): 0727-0727  
DOI: 10.1055/s-2007-968618
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Alkylation of Aldehydes with Fluorous TADDOL Analogue

Contributor(s): Mark Lautens, Frédéric Ménard
Y. S. Sokeirik, H. Mori, M. Omote, K. Sato, A. Tarui, I. Kumadaki, A. Ando*
Setsunan University, Hirakata, Japan
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

The application of L4 to the ligand-accelerated asymmetric methylation of aldehydes gives excellent results for a variety of aryl and hetero­aryl acceptors. The highly fluorinated ligand L4 is based on the TADDOL framework (D. Seebach et al. Angew. Chem. Int. Ed. 2001, 40, 92-138). The perfluorinated alkyl chains allow recycling of the L4 ligand by simple crystallization from cold toluene. The recovered ligand gave reproducibly high yields, and was used in four recycles before showing decreased selectivity.