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Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols

Organic Letters, ISSN: 1523-7052, Vol: 23, Issue: 16, Page: 6262-6266
2021
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Article Description

The first stereoselective propargylic dearomatization of 2-naphthol derivatives is reported using a chiral CuII-L10 complex. The reaction shows chemodivergent reactivity and produced propargyl dearomatization and etherification product for differently substituted 2-naphthols. Both the reactions generate the desired products in high yields with excellent chemo- and stereoselectivities (up to 99% ee, dr = 9:1) by using only 2 mol % catalyst loading. Dearomatization products contain a contiguous all-carbon quaternary-tertiary stereocenter and a terminal alkyne functionality.

Bibliographic Details

Das, Braja Gopal; Shah, Sadhna; Das, Arko; Singh, Vinod K

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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