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

• Matsuo, Junichi

• Hattori, Yu

• Hashizume, Mio

• Ishibashi, Hiroyuki

抄録

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 α-silyl alcohols were obtained in high yields with high ees. © 2010 Elsevier Ltd. All rights reserved.

金沢大学医薬保健研究域薬学系

収録刊行物

• Tetrahedron

  Tetrahedron 66 (32), 6062-6069, 2010-01-01

  Elsevier

詳細情報

• CRID: 1050845760884207872
• NII論文ID: 120002314576
• NII論文ID: 120002439390
• NII書誌ID: AA00861787
• ISSN: 00404020
• HANDLE: 2297/25207
• HANDLE: 2297/24794
• Web Site: https://kanazawa-u.repo.nii.ac.jp/records/15336
• Web Site: https://kanazawa-u.repo.nii.ac.jp/records/15341
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles
  • KAKEN