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Synfacts 2007(7): 0729-0729  
DOI: 10.1055/s-2007-968674
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Methyl Carbinols Using Fluorous Ligand

Contributor(s): Hisashi Yamamoto, Marina Naodovic
M. Omote, N. Tanaka, A. Tarui, K. Sato, 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 novel fluorous ligand enables the installation of a methyl group to aldehydes via highly stereoselective, Ti(IV)-mediated addition of Me2Zn. High fluorine contents (60% by weight) enable its recovery by standard fluorous techniques. Perfluoro groups provide increased stability of hydroxyl groups and in this way further the recycling of the ligand.