Catalytic asymmetric Mannich reactions of glycine derivatives with imines. A new approach to optically active α,β-diamino acid derivatives

Journal of Organic Chemistry

Volumn 68, Issue 7, 2003, Pages 2583-2591

  Bernardi, Luca ^a   Gothelf, Aase S ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

MANNICH REACTIONS;

CATALYSTS; COMPLEXATION; COPPER;

AROMATIC COMPOUNDS;

AMINO ACID DERIVATIVE; COPPER COMPLEX; GLYCINE; IMINE;

AMINO ACID ANALYSIS; ARTICLE; CALCULATION; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; OPTICAL ROTATION; REACTION ANALYSIS;

AMINO ACIDS; CATALYSIS; GLYCINE; IMINES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0037419152     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026766u     Document Type: Article

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71. 2 in THF at room temperature has been found to be able to remove the N-tosyl substituent from β-lactams: see ref 15m.
72. We have previously postulated that highly activated imines such as the N-tosyl-α-imino ester 3j coordinate to the catalyst in various types of addition reactions to this imine: see e.g. ref 15j.
73. The structures have been optimized by using PM3 calculations applying the PC-Spartan program.
74. The heat of formation calculated for 10a and 11a is -10.9 and -11.1 kcal/mol, respectively. For 10b and 11b, the calculated heat of formation values are -39.2 and -26.8 kcal/mol, respectively.
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