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Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis

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posted on 09.11.2007 by Santos Fustero, Begoña Fernández, Juan F. Sanz-Cervera, Natalia Mateu, Silvia Mosulén, Rodrigo J. Carbajo, Antonio Pineda-Lucena, Carmen Ramírez de Arellano
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.

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