Reactions of Donor–Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert | Zendy

Lücht Alexander | Zendy; Patalag Lukas J. | Zendy; Augustin André U. | Zendy; Jones Peter G. | Zendy; Werz Daniel B. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Reactions of Donor–Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert

Author(s) -

Lücht Alexander,

Patalag Lukas J.,

Augustin André U.,

Jones Peter G.,

Werz Daniel B.

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201703732

Subject(s) - umpolung , chemistry , nucleophile , lewis acids and bases , electrophile , catalysis , ring (chemistry) , photochemistry , medicinal chemistry , lewis acid catalysis , redox , organic chemistry

Reactions of 2‐arylcyclopropane dicarboxylates with naphthoquinones are reported. The key feature was the use of catalytic amounts of SnCl 2 , which acts as both an electron donor and a Lewis acid. By an in situ umpolung of naphthoquinone the formerly electrophilic species is converted into a nucleophile that is able to trigger the ring‐opening of the three‐membered ring with formation of a new C−C bond. Treatment of these products with base under oxidative conditions resulted—through loss of methyl formate—in cyclopentannulated products with fully conjugated π systems exhibiting intensive absorptions in the visible range.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research