Asymmetric fluorination of α-aryl acetic acid derivatives with the catalytic system NiCl2-binap/R3SiOTf/2,6-lutidine

Angewandte Chemie - International Edition

Volumn 46, Issue 28, 2007, Pages 5435-5439

  Suzuki, Toshiaki ^a   Hamashima, Yoshitaka ^a   Sodeoka, Mikiko ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Asymmetric catalysis; Carboxylic acid derivatives; Fluorination; Lewis acids; Nickel

Indexed keywords

ASYMMETRIC CATALYSIS; BINARY SYSTEMS; CARBOXYLIC ACID DERIVATIVES; LEWIS ACIDS;

ACETIC ACID; BINARY MIXTURES; CATALYST ACTIVITY; DERIVATIVES; FLUORINATION; NICKEL COMPOUNDS;

CARBOXYLIC ACIDS;

2,6 DIMETHYLPYRIDINE; 2,6-LUTIDINE; ACETIC ACID DERIVATIVE; FLUORINE DERIVATIVE; NICKEL; NICKEL CHLORIDE; ORGANOMETALLIC COMPOUND; OXIDE; PYRIDINE DERIVATIVE; SILICON DERIVATIVE; SILICON OXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETIC ACIDS; CATALYSIS; FLUORINE COMPOUNDS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; OXIDES; PYRIDINES; SILICON COMPOUNDS; STEREOISOMERISM;

EID: 34447554613     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701071     Document Type: Article

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49. 2 (3 equiv) was used as an external activator to form an oxonium intermediate from methyl orthoformate.
50. II gave almost racemic products under similar conditions.
51. 2 did not proceed at all.
52. [17]
53. 2 at room temperature.
54. 2NEt, pyridine, and 2,6-di(tert-butyl)pyridine, led to less satisfactory results.
55. Details of these experiments will be discussed in a full paper.
56. [10a] (Chemical Equation Presented)