Synthesis of Axially Dissymmetric Ligands with Two Chiral Centers of Perfluoroalkyl Carbinol Moiety, and Their Application to Asymmetric Syntheses

Author(s): Masaaki Omote, Kazuyuki Sato, Akira Ando, Itsumaro Kumadaki.

Journal Name: Current Organic Synthesis

Volume 4 , Issue 2 , 2007

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Abstract:

We have synthesized (Ra*)-(R*)2-2,2-bis(1-hydroxy-1H-perfluoroalkyl)biphenyls, axially dissymmetric ligands with two chiral centers. Their titanium complex induces high enantioselectivity in the reaction of an aldehyde with dialkylzinc. Other reactions of these ligands as a chiral ligand or a chiral auxiliary will be presented. The ligand with long perfluoroalkyl sidechains can be extracted selectively with a fluorous solvent such as perfluorohexane. This enables it to be recovered easily by a fluorous phase separation technique and to be used repeatedly.

Keywords: Axial dissymmetry, ligand, chiral center, perfluoroalkyl, carbinol, fluorous, recycling

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Article Details

VOLUME: 4
ISSUE: 2
Year: 2007
Page: [137 - 150]
Pages: 14
DOI: 10.2174/157017907780598880
Price: $58

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