Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group

The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C–H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH(2) auxiliary embedded in the substrate provided excellent level...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Jinhee, Sim, Mikyung, Kim, Namhoon, Hong, Sungwoo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659170/
https://www.ncbi.nlm.nih.gov/pubmed/29511524
http://dx.doi.org/10.1039/c5sc01137j
Descripción
Sumario:The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C–H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH(2) auxiliary embedded in the substrate provided excellent levels of asymmetric induction (diastereomeric ratio of up to 72 : 1) in the Pd(ii)-catalyzed β-methylene C(sp(3))–H bond activation of cyclopropanes and cross-coupling with aryl iodides.

Ejemplares similares