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

Manabu Hatano, Tomokazu Mizuno, Kazuaki Ishihara*

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

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

DOI: 10.1055/s-0030-1258129

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Abstract

A refined version of Charette's procedure for the preparation of zinc reagents from Grignard reagents minimizes the side reactions in the subsequent catalytic, enantioselective n-alkyl addition of commercially unavailable di(n-alkyl)zinc reagents to aldehydes and ketones.

see article for more examples

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

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

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Key Words

1,2-addition, green chemistry, asymmetric catalysis, ginnol, Grignard reagent, zinc

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ID: J60-Y2010-2250