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

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

Volume: 4 Issue: 2

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

Affiliation:

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

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.

Cite this article as:

Omote Masaaki, Sato Kazuyuki, Ando Akira and Kumadaki Itsumaro, Synthesis of Axially Dissymmetric Ligands with Two Chiral Centers of Perfluoroalkyl Carbinol Moiety, and Their Application to Asymmetric Syntheses, Current Organic Synthesis 2007; 4 (2) . https://dx.doi.org/10.2174/157017907780598880