Journal
ORGANIC LETTERS
Volume 24, Issue 31, Pages 5693-5697Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02072
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Funding
- National Natural Science Foundation of China [21831045]
- Natural Science Foundation of Jilin Province [20190201070JC]
- Taishan Scholar Youth Program of Shandong Province
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In this study, a Lewis-base-catalyzed three-component electrophilic thiofunctionalization was developed for the synthesis of trisubstituted chromanes. This metal-free protocol offers high trans-diasteroselectivity and a unique substitution pattern, enabling access to the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.
A Lewis-base-catalyzed three-component electrophilic thiofunctionalization of cyclopropene with phenol is developed to furnish various trisubstituted chromanes in high trans-diasteroselectivity. This metal-free protocol is easy to scaleup, offers a unique 2,2,3-substitution pattern, and delivers chromanes with diversified core substitution patterns. The unprecedented tolerance of strong electron-withdrawing substituents at the phenol renders the protocol indispensable to access the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.
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