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Asymmetric Synthesis of Fluorinated Cyclic β-Amino Acid Derivatives through Cross Metathesis

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posted on 2006-09-28, 00:00 authored by Santos Fustero, María Sánchez-Roselló, Juan F. Sanz-Cervera, José Luis Aceña, Carlos del Pozo, Begoña Fernández, Ana Bartolomé, Amparo Asensio
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding β-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (−)-8-phenylmenthol as a chiral auxiliary.

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