Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

TETRAHEDRON

卷:66

Article

Matsuo, Jun-ichi¹  Hattori, Yu¹  Hashizume, Mio¹  Ishibashi, Hiroyuki¹ 

[1] Kanazawa Univ, Sch Pharmaceut Sci, Inst Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan

关键词: Asymmetric reduction;    Ketone;    Acyl silane;    Meerwein-Ponndorf-Verley reduction;    Oppenauer oxidation;   

DOI  :  10.1016/j.tet.2010.06.012

来源: Elsevier

【 摘 要 】

Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99% ee) was observed in the reduction of tert-alkyl ketones. Asymmetric reduction of acyl silanes using chiral anti-pentane-2,4-diol and DNBSA proceeded efficiently in the absence of octanethiol and the corresponding a-silyl alcohols were obtained in high yields with high ees. (c) 2010 Elsevier Ltd. All rights reserved.

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