Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis |
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Authors: | Fustero Santos Sanchez-Roselló María Sanz-Cervera Juan F Aceña José Luis Del Pozo Carlos Fernandez Begoña Bartolomé Ana Asensio Amparo Ramírez de Arellano Carmen |
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Institution: | Departamento de Química Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es |
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Abstract: | 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 beta-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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