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Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes

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Abstract

An efficient asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols and in situ generated ortho-quinone methides with chiral phosphoric acid as the catalyst was developed. This reaction enables the highly enantioselective synthesis of chiral polysubstituted chromanes bearing multiple contiguous stereogenic centers in excellent yields and stereoselectivities (up to 99% yield, >95 : 5 dr and >99% ee).

Graphical abstract: Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes

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Publication details

The article was received on 23 Oct 2019, accepted on 03 Dec 2019 and first published on 04 Dec 2019


Article type: Communication
DOI: 10.1039/C9CC08316B
Chem. Commun., 2020, Advance Article

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    Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes

    Y. You, T. Li, S. Yuan, K. Xie, Z. Wang, J. Zhao, M. Zhou and W. Yuan, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08316B

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