Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis

The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-11, Vol.72 (23), p.8716-8723
Main Authors: Fustero, Santos, Fernández, Begoña, Sanz-Cervera, Juan F, Mateu, Natalia, Mosulén, Silvia, Carbajo, Rodrigo J, Pineda-Lucena, Antonio, Ramírez de Arellano, Carmen
Format: Article
Language:English
Subjects:
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Chemistry
Crystallography, X-Ray
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Hydrocarbons, Fluorinated - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Macrocyclic Compounds - chemical synthesis
Models, Molecular
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the α-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo701484w