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Enantioselective Rh-Catalyzed Carboacylation of C?N Bonds via C-C Activation of Benzocyclobutenones.

ABSTRACT: Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C?N bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.

SUBMITTER: Deng L

PROVIDER: S-EPMC4884656 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C-C Activation of Benzocyclobutenones.

Deng Lin L Xu Tao T Li Hongbo H Dong Guangbin G

Journal of the American Chemical Society 20151228 1

Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C═N bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of t ...[more]

PMID: 26674855

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