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Issue 3, 2020
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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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Supplementary files

Article information


Submitted
23 Oct 2019
Accepted
03 Dec 2019
First published
04 Dec 2019

Chem. Commun., 2020,56, 439-442
Article type
Communication

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, 56, 439
DOI: 10.1039/C9CC08316B

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