A Practical Synthesis of C2-Symmetric Chiral Binaphthyl Ketone Catalyst

Masahiko Seki; Shin-ichi Yamada; Tooru Kuroda; Ritsuo Imashiro; Toshiaki Shimizu

doi:10.1055/s-2000-8197

Synthesis 2000; 2000(12): 1677-1680
DOI: 10.1055/s-2000-8197

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A Practical Synthesis of C ₂-Symmetric Chiral Binaphthyl Ketone Catalyst

Masahiko Seki^* , Shin-ichi Yamada, Tooru Kuroda, Ritsuo Imashiro, Toshiaki Shimizu

^*Product & Technology Development Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532-8505, Japan; Fax +81 (6) 63 00 28 16; E-mail: m-seki@tanabe.co.jp

Abstract

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A practical synthesis of 11-membered C ₂-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (±)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(±)-6] was efficiently resolved by (R)-(-)-1-cyclohexylethylamine to give (R)-6 in > 99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 °C provided the desired chiral ketone (R)-1 in 61-63% yield without need for high dilution techniques.

catalysts - asymmetric epoxidation - dioxiranes - macrocycles - optical resolution

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A Practical Synthesis of C 2-Symmetric Chiral Binaphthyl Ketone Catalyst

A Practical Synthesis of C ₂-Symmetric Chiral Binaphthyl Ketone Catalyst