Highly selective enzymatic kinetic resolution of primary amines at 80°C: A comparative study of carboxylic acids and their ethyl esters as acyl donors

Journal of Organic Chemistry

Volumn 72, Issue 18, 2007, Pages 6918-6923

  Nechab, Malek ^a   Azzi, Nadia ^a   Vanthuyne, Nicolas ^a   Bertrand, Michèle ^a   Gastaldi, Stéphane ^a   Gil, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL DONORS; AMINOLYSIS; BENZYLIC AMINES; ETHYL ESTERS; LAURAMIDE;

CARBOXYLIC ACIDS; ENANTIOMERS; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ESTERS; REACTION KINETICS;

AMINES;

2 AMINO 4 PHENYLBUTANE; ALIPHATIC AMINE; AMINE; BENZYL DERIVATIVE; BUTANE; CARBOXYLIC ACID DERIVATIVE; LAURAMIDE; LAURIC ACID; LIPASE B; UNCLASSIFIED DRUG;

ACYLATION; AMINOLYSIS; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ENANTIOMER; ENZYME KINETICS; REACTION TIME; RECYCLING;

AMINES; CARBOXYLIC ACIDS; ESTERS; HEPTANES; KINETICS; LAURIC ACIDS; LIPASE; MOLECULAR STRUCTURE; TEMPERATURE;

EID: 34548817885     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071069t     Document Type: Article

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97. For comparative data for the resolution of amine 1, see refs 10f, 12b,d; for amine 2, see refs 10g, 12c, 13b, 15c; for amine 3, see refs 10g, 13b; for amine 4, see refs 12c, 13b,c; for amine 8, see ref 15b; for amine 9, see ref 13g; for amine 10, see ref 10f; for amine 11, see refs 10g, 12a,d, 13b,c,g, 14c, 15b,d; for amine 12, see refs 10g, 13a,e,g, 14c; for amine 13, see refs 12c, 13a,e; for amine 14, see refs 12b,c,d, 15b.
98. Boiling points: 2 (63°C), 2 (142°C), 5 (154°C), heptane (102°C).
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101. In the DKR experiments reported in ref 5, the use of lauric acid as acylating agent led to transform rac-1 into (R)-1e (71% yield and ee > 99%); the use of ethyl laurate led to the same amide in 70% isolated yield and 99% ee.