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Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C-H functionalization.

ABSTRACT: We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.

SUBMITTER: Chen J

PROVIDER: S-EPMC8356817 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols <i>via</i> a sequential reduction/C-H functionalization.

Chen Jun J Shi Zhan Z Li Chunyu C Lu Ping P

Chemical science 20210705 31

We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyll ...[more]

PMID: 34447553

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