The catalytic production of chiral amides from readily available unactivated internal alkenes remains a significant challenge in synthetic chemistry.In this work,we developed a highly enantioselective hydroaminocarbon...The catalytic production of chiral amides from readily available unactivated internal alkenes remains a significant challenge in synthetic chemistry.In this work,we developed a highly enantioselective hydroaminocarbonylation procedure for nonactivated internal alkenes and a wide range ofα-chiral amides were produced effectively with exceptional enantioselectivities using copper as the catalyst.This method is compatible with both symmetric and asymmetric internal alkenes,as well as various hydroxylamine electrophiles,demonstrating wide substrate scope and broad functional group tolerance.The established catalytic system showcases remarkable enantioselective performance in the asymmetric hydroaminocarbonylation of challenging substrates,such as the methyl-ethylα-chiral amide synthesis from trans-2-butene,despite the minimal steric difference between the methyl and ethyl group.This work represents important progress in the field of asymmetric hydroaminocarbonylation and offers a useful tool for the production of valuableα-chiral amide compounds from readily available internal alkenes.展开更多
基金support provided by the National Key R&D Program of China(grant no.2023YFA1507500)the National Natural Science Foundation of China(grant no.22302198)the International Partnership Program of Chinese Academy of Sciences(grant no.028GJHZ2023045FN).
文摘The catalytic production of chiral amides from readily available unactivated internal alkenes remains a significant challenge in synthetic chemistry.In this work,we developed a highly enantioselective hydroaminocarbonylation procedure for nonactivated internal alkenes and a wide range ofα-chiral amides were produced effectively with exceptional enantioselectivities using copper as the catalyst.This method is compatible with both symmetric and asymmetric internal alkenes,as well as various hydroxylamine electrophiles,demonstrating wide substrate scope and broad functional group tolerance.The established catalytic system showcases remarkable enantioselective performance in the asymmetric hydroaminocarbonylation of challenging substrates,such as the methyl-ethylα-chiral amide synthesis from trans-2-butene,despite the minimal steric difference between the methyl and ethyl group.This work represents important progress in the field of asymmetric hydroaminocarbonylation and offers a useful tool for the production of valuableα-chiral amide compounds from readily available internal alkenes.
