Highly Active Chiral Phosphoramide-Zn(II) Complexes as Conjugate Acid-Base Catalysts for Enantioselective Organozinc Addition to Ketones

Manabu Hatano, Takashi Miyamoto and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan, Email: ishiharacc.nagoya-u.ac.jp

M. Hatano, T. Miyamoto, K. Ishihara, Org. Lett., 2007, 9, 4535-4538.

DOI: 10.1021/ol702074a

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Abstract

In a highly efficient enantioselective organozinc addition to ketones, chiral phosphoramide-Zn(II) complexes serve as conjugate Lewis acid-Lewis base catalysts. From a variety of nonactivated aromatic and aliphatic ketones, the corresponding optically active tertiary alcohols were obtained in high yields with high enantioselectivities under mild reaction conditions.

see article for more examples

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A Concise Synthesis of (S)-(+)-Ginnol Based on Catalytic Enantioselective Addition of Commercially Unavailable Di(n-alkyl)zinc to Aldehydes and Ketones

M. Hatano, T. Mizuno, K. Ishihara, Synlett, 2010, 2024-2028.

3,3'-Diphosphoryl-1,1'-bi-2-naphthol-Zn(II) Complexes as Conjugate Acid-Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes

M. Hatano, T. Miyamoto, K. Ishihara, J. Org. Chem., 2006, 71, 6474-6484.

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Key Words

arylation, alkylation

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ID: J54-Y2007-3390