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Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.

ABSTRACT: Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon-hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon-hydrogen bond and the difficult enantiofacial discrimination of two sterically similar aryl substituents. Here we disclose an N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes. Our method allows for highly enantioselective transformation of diaryl methanes and quick access to benzimidazole fused lactams.

SUBMITTER: Chen Q

PROVIDER: S-EPMC6263396 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.

Chen Qiao Q Zhu Tingshun T Majhi Pankaj Kumar PK Mou Chengli C Chai Huifang H Zhang Jingjie J Zhuo Shitian S Chi Yonggui Robin YR

Chemical science 20180918 46

Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon-hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon-hydrogen bond and the difficult enantiofacial discrimination of two sterically similar aryl substituents. Here we disclose an N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hete ...[more]

PMID: 30595836

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