Stereoselective reduction of ketones by histidine-alkoxysilane complexes: The role of imidazole in nucleophilic substitution at silicon

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3507-3510

  LaRonde, Frank J ^a   Brook, Michael A ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HISTIDINE; IMIDAZOLE; KETONE DERIVATIVE; SILANE DERIVATIVE; SILICON;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033617419     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00543-2     Document Type: Article

References (19)

1. 1 Fax: +1905 522 2509; Email: mabrook@mcmaster.ca
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19. 16 General experimental procedure for preparation of Mosher esters (for (S)-1-phenylethanol)): (S)-1-phenylethanol (2 mg, 0.02 mmol) and MTPA-Cl (+) (4 mL, 0.02 mmol) were mixed with carbon tetrachloride (3 drops) and dry pyridine (3 drops). The reaction mixture was allowed to stand in a stoppered flask for 12 h at ambient temperature. Water (1 mL) was added and the reaction mixture transferred to a separatory funnel and extracted with ether (20 mL). The ether solution, after washing successively with HC1 (1M, 20 mL), and saturated sodium carbonate solution (20 mL), and water (20 mL) was dried with sodium sulfate, filtered and solvent was removed in vacuo. The residue was dissolved in deuterated chloroform for NMR analysis. The integrations(s) of the hydrogen on the carbon bearing the hydroxyl group was used as a measure to assess the enantioselection.