A DFT study of the mechanisms and regio- and stereochemistry of the Lewis acid-catalyzed reactions of 5-alkoxyoxazoles with aldehydes: Aryl substitution at the 2-position of 5-alkoxyoxazole is critical to the formation of 4-alkoxycarbonyl-2-oxazoline

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 421-432

  Yu, Zhi Xiang ^a,b   Wu, Yun Dong ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ACTIVATION ENERGY; ALDEHYDES; CATALYSIS;

LEWIS ACIDS;

STEREOCHEMISTRY;

ALDEHYDE; LEWIS ACID; OXAZOLE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENERGY; GEOMETRY; STEREOCHEMISTRY;

EID: 0037462388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0263317     Document Type: Article

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52. 3 and the carbonyl carbon of aldehyde. This artificial phenomenon can be avoided in solvent due to the dampened interaction between the two reactants. As shown later in reaction VI, such a precursor complex 66 in reaction VI can be located in the gas phase.
53. 2 bond forming in the C-trans path in the reaction V were not successful. We think that RC transition state 77 should exist with very low activation barrier given the fact that all the RC steps located for reactions IV and V have very low activation barriers.
54. 2. Here we see again that the rate-determining step for the manifold C is the RO step.
55. 4