Catalytic asymmetric synthesis of (S)-acetophenone cyanohydrin under high pressure

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6669-6672

  Choi, Michael C K ^a   Chan, S S ^a   Matsumoto, Kiyoshi ^b  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYPERBARISM; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030828431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01561-X     Document Type: Article

References (19)

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15. 2 (20ml) and 0.5 M HCL (20 ml). The usual extraction work-up to give a mixture of acetophenone and silylated acetophenone cyanohydrin from which the % yield was determined. The product was stirred in a mixture of 2 M HCl (20ml) and ethyl acetate (40 ml) for 3 h at room temperature. The usual extraction work-up and silica gel column chromatography (hexane: ethyl acetate, 5:1) of the residue gave a mixture of acetophenone and its cyanohydrins.
16. The cyanohydrin was hydrolyzed with conc. HCl to the corresponding 2-hydroxy-2-phenylpropionic acid and compared with the optical rotation value of the optically active acid (No. 8692) from Lancaster catalogue 95/96.
17. Enantiomeric excess was determined using G.C. on a WCOT fused silica 25m × 0.25mm coating CP chirasil-Dex capillary column after derivatization of the cyanohydrin with acetic anhydride.
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