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CBS催化硼烷胺配合物不对称还原法制备(S)-3-氯-1-苯基-1-丙醇 被引量:4

Asymmetric Synthesis of(S)-3-Chloro-1-phenyl-1-propanol Using Borane Amine Complex-CBS as Catalyst
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摘要 分别以R-α,α-二苯基脯氨醇、(1R,2S)-2-氨基-1,2-二苯基乙醇和(1R,2S)-(-)-1-氨基-2-茚醇为催化剂,以多种硼烷胺配合物为还原剂,由β-氯代苯乙酮不对称合成(S)-3-氯-1-苯基-1-丙醇,收率88.3%~93.8%,e.e.值为81.6%~87.7%。用硼烷胺配合物代替硼烷-THF和硼烷二甲硫醚,稳定性好,容易计量和安全操作。 (S)-3-Chloro-1-phenyl-1-propanol was synthesized asymmetrically by using catalysts (R)-α,α-diphenyl-2-pyrrolidinemethanol, (1R,2S)-2-amino-1,2-diphenylethanol and (1R,2R)-1-amino-2-indanol with amine borane complexes, with a yield of 88.3%~93.8%, ee% 81.6~87.7. These amine borane complexes are more stable and safe than the borane-tetrahydrofuran complex and borane-methyl sulfide complex.
出处 《应用化学》 CAS CSCD 北大核心 2012年第9期1087-1089,共3页 Chinese Journal of Applied Chemistry
关键词 硼烷胺配合物 CBS催化 (S)-氯苯基丙醇 氟西汀 borane amine complex, CBS catalyst, (S)-chlorophenylpropanol ,fluoxetine
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  • 1Corey E J, Bakshi R K, Shibata S. Highly Enantioselective Borane Reduction of Ketones Catalyzed by Chiral Oxazaborolidines. Mechanism and Synthetic Implications[J]. J Am Chem Soc,1987,109(18) :5551-5553.
  • 2Corey E J, Helal C J. Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method[ J]. Angew Chem lnt Ed,1998,37:1986-2012.
  • 3Salunkhe A M, Burkhardt E R. Highly Enantioselective Reduction of Prochiral Ketones with N, N-Diethylaniline. Borane (DEANB) in Oxazaborolidine-catalyzed Reductions [ J ]. Tetrahedron Lett, 1997,38 (9) : 1523-1526.
  • 4Salunkhe A M, Burkhardt E R. N,N-Diethylaniline. Borane, an Efficient Reducing Agent for Reduction of RepreSentative Functional Groups [ J ]. Tetrahedron Lett, 1997,38 ( 9 ) : 1519 - 1522.
  • 5Brown H C, Murray L T. Effect of Structure on the Reactivities of Representative Borane-Amine Complexes in Typical Reactions Such as Hydrolysis, Hydroboration, and Reduction [ J ]. Inorg Chem, 1984,23 ( 18 ) : 2746-2753.
  • 6Cho B T,Shin S H. Highly Enantioselective Synthesis of Multifunctionalized Allylic Building Blocks via Oxazaborolidine- catalyzed Borane Reduction [ J ]. Tetrahedron, 2005,61 (29) :6959-6966.
  • 7Corey E J, Reichard G A. Enantioselective and Practical Syntheses of R- and S-Fluoxetines[ J]. Tetrahedron Lett, 1989,30 (39) :5207-5210.
  • 8Padiya K, Gagare P, Gagare M, et al. Asymmetric Synthesis of (R)-Fluoxetine:A Practical Approach Using Recyclable and in-situ Generated Oxazaborolidine Catalyst [ J ]. Chinese J Chem,2009,27 ( 6 ) : 1137-1140.
  • 9Lapisa A A M, de Fotimaa A, Martinsb J E D,et al. Asymmetric Reduction of Prochiral Ketones Using in situ Gdnerated Oxazaborolidine Derived from ( IS, 2S, 3R, 4R )-3-Amino-7, 7-dimethoxynorboman-2-ol. An efficient Synthesis of Enantiopure (R) -Tomoxetine [ J ]. Tetrahedron Lett, 2005,46 ( 3 ) :495-498.
  • 10Brown H C. Borane-N, N-dialkylaniline Hydroboration Agents : US,005543569, A [ P ] , 1996-08-06.

同被引文献47

  • 1侯瑞鹏,李健,李昭夷,冯起庆,张蓓,丁兆权,王亚申.早泄标记物的应用研究[J].临床泌尿外科杂志,2020,0(1):10-13. 被引量:3
  • 2聂映,毕小玲,尤启冬.阿瑞吡坦[J].中国新药杂志,2006,15(3):238-239. 被引量:16
  • 3龚大春,李德莹,田毅红,韦萍,欧阳平凯.固定化脂肪酶催化合成(R)-3-氯-1-苯丙醇[J].中国医药工业杂志,2007,38(11):758-759. 被引量:3
  • 4Herbert C.Brown.Process For Preparing Optically Active Haloalohols: United States Patent,364875[P]. 1990-04-17.
  • 5Kaoru Nakamura , Rio Yamanaka.Light-mediated regulation of asymmetric reduction of ketones by a cyanobacterium[J].Tetrahedron: Asymmetry,2002,13:2529-2533.
  • 6Cheng C., Ma J.H.,Enantioselective synthesis of S-(-)- 1-Phenythanol in candida utilis semi-fed-bathtch cultures[J].Pro. Biochem., 1996, 31: 119-124.
  • 7Zhimin Ou,Jiangping Wu, Asymmetric reduction of chloroacetophenones to produce chiral alcohols with microorganisms[J].Korean J.Chem.Eng.,2008,25( 1 ), 124-128.
  • 8k.Faber.Biotransformations in organic chemistry[M]. Beijing: Beijing Publishing Corporation, 1999.
  • 9Gensheng Yang, Zhimin Ou , et al. Asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-l-phenylpropanol using immobilized Saccharomyces cerevisiae CGMCC 2266 cells[J]. Journalof Molecular Catalysis B: Enzymatic, 2009,57: 83-88.
  • 10F. Baldassarre, G. Bertoni,, et al.Preparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst[J]. Journal of Molecular Catalysis B: Enzymatic,2000(11):55 -58.

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