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

[ Vol. 4 , Issue. 2 ]

Author(s):

Masaaki Omote, Kazuyuki Sato, Akira Ando and Itsumaro Kumadaki   Pages 137 - 150 ( 14 )

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

Affiliation:

Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho,Hirakata, Osaka 573-0101, Japan.



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