Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts

Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in mo...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (15), p.5709-5713
Main Authors: Huang, Jing-Kai, Shia, Kak-Shan
Format: Article
Language:English
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Letter
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Summary:Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01807