Recyclable fluorous chiral ligands and catalysts: asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by fluorous BINOL-Ti complexes

Yutaka Nakamura*, Seiji Takeuchi, Kazuo Okumura, Yoshiaki Ohgo and Dennis P. Curran

*Niigata College of Pharmacy, 5-13-2 Kamishin'ei cho, Niigata 950-2081, Japan, Email: Nakamuraniigata-pharm.ac.jp

Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron, 2002, 58, 3963-3969.

DOI: 10.1016/S0040-4020(02)00245-4

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Abstract

Fluorous chiral BINOLs were prepared and used as the ligands for the titanium catalyzed asymmetric addition of Et₂Zn to aromatic aldehydes. Products were isolated by simple fluorous-organic biphase and fluorous solid phase extraction techniques with similar enantioselectivities to that attained in the non-fluorous system. The recovered FBINOLs can be recycled.

see article for more reactions

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Key Words

Addition reactions, asymmetric reactions, fluorine and compounds, perfluoroalkyl compounds

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ID: J72-Y2002-090