Bulletin of the Korean Chemical Society

  • 제15권1호
  • /
  • Pages.53-57
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  • 1994
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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A Direct Comparison Study of Asymmetric Borane Reduction of C=N Double Bond Mediated by Chiral Oxazaborolidines

  • Cho Byung Tae (Department of Chemistry, Hallym University) ;
  • Ryu, Mi Hae (Department of Chemistry, Hallym University) ;
  • Chun Yu Sung (Department of Chemistry, Hallym University) ;
  • Dauelsberg Ch. (Fachbereich Chemie, Universit$\"{a}$t Oldenburg) ;
  • Wallbaum Sabine (Fachbereich Chemie, Universit$\"{a}$t Oldenburg) ;
  • Martens Jurgen (Fachbereich Chemie, Universit$\"{a}$t Oldenburg)
  • 발행 : 1994.01.20
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초록

A comparison study on asymmetric borane reduction of ketoxime ethers and N-substituted ketimines possesing C = N double bond mediated by the selected chiral oxazaborolidines (1-6) was investigated. Thus, an aromatic ketoxime O-alkyl ether acetophenone oxime O-methyl ether was reduced to the corresponding amine (1-phenylethylamine 8a) with optical yields, such as 58% ee with 1, 86% ee with 2, 3% ee with 3, 99% ee with 4, 60% ee with 5, and 73% ee with 6. However, the reduction of an aliphatic ketoxime derivative 2-heptanone oxime O-methyl ether provided low optical inductions (7-13% ee). For ketoxime O-trimethylsilyl ethers, the reduction of acetophenone O-trimethylsilyl ether afforded 8a with optical yields which were 90% ee with 1, 40% ee with 2, 2% ee with 3, 62% ee with 4, 5% ee with 5, and 60% ee with 6. The reduction of 2-heptanone O-trimethylsilyl ether also gave the product amine with low optical yields (10-40% ee). In the case of N-substituted ketimines, the reduction of acetophenone N-phenylimine afforded the corresponding amine with 79% ee, 78% ee, 9% ee, 73% ee, 78% ee and 67% ee using 1, 2, 3, 4, 5, and 6, respectively, whereas low optical inductions (5-18% ee) for 2-heptanone N-phenylimine were achieved.

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참고문헌

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피인용 문헌

  1. Rationalising the effect of reducing agent on the oxazaborolidine-mediated asymmetric reduction of N-substituted imines vol.45, pp.4, 2004, https://doi.org/10.1016/j.tetlet.2003.11.021
  2. Stereoselective synthesis of new monoterpene β-amino alcohols vol.20, pp.13, 1994, https://doi.org/10.1016/j.tetasy.2009.06.007
  3. Conformational Analysis and Optical Rotation of Carene β-Amino Alcohols: A DFT Study vol.2009, pp.27, 1994, https://doi.org/10.1002/ejoc.200900474