Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5195-5198

  Masui, Moriyasu ^a   Shioiri, Takayuki ^b  

^a SHIONOGI AND CO LTD   (Japan)

^b NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Asymmetric reactions; Ketones; Oximes; Reduction

Indexed keywords

AMINOALCOHOL; BORANE DERIVATIVE; ETHER DERIVATIVE; OXIME; PINENE; PROLINE;

ARTICLE; CHIRALITY; ENANTIOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032537682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01019-3     Document Type: Article

References (20)

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10. 3 in acetone, (c) tert-butyldimethylchlorosilane and imidazole in DMF, (d) tert-butyldiphenylchlorosilane and imidazole in DMF, or (e) trityl chloride and triethylamine in dichloromethane.
11. 9,14
12. 4 and evaporated. The crude material was purified by column chromatography to gave the desired product as a mixture of diastereomers.
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14. 11. The borane reduction of acetophenone using the catalyst generated in situ from 0.1 eq of (2R, 3R)-3-amino-2-butanol (9) and borane-dimethyl sulfide complex afforded (R)-2-phenylethanol in only 64 % ee.
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18. 15. To the resulting mixture obtained in the procedure described in note 8 was added benzoyl chloride (10 mmol), and the mixture was stirred for 0.5 h at room temperature. After the addition of methanol (15 ml), the mixture was stirred for 5∼15 h at room temperature. Evaporation of the solvent gave a crude product, which was isolated by filtration and/or extraction. Purification by column chromatography afforded N-benzoyl-1,2-amino alcohol as a mixture of diastereomers.
19. 16. (1R,2S)-Norephedrine and (1R,2S)-2-amino-1,2-diphenylethanol were commercially available from Aldrich Chemical Company, Inc. Optically active 2-amino-1-tetralol was synthesized as described in reference 5. Optically active 1-amino-1-phenyl-2-propanol and 2-amino-1-indanol were prepared as described, respectively, in: (a) Zietlow, A.; Steckhan, E. J. Org. Chem. 1994, 59, 5658.
20. (b) Dornhege, E. Liebigs Ann. Chem. 1971, 743, 42.