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Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2 + 1] annulation of para-quinone methides with bromides

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Abstract

An efficient sulfide-catalyzed [2 + 1] annulation of para-quinone methides (p-QMs) with diverse bromides has been achieved. This catalytic strategy provides an efficient and straightforward protocol for accessing a variety of spiro-cyclopropanyl-cyclohexadienone compounds in good to excellent yields (64% to 96% yields) with outstanding diastereoselectivities (>20 : 1 dr), displaying good functional group tolerance as well as gram-scale capacity.

Graphical abstract: Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2 + 1] annulation of para-quinone methides with bromides

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Article information


Submitted
15 Apr 2020
Accepted
19 May 2020
First published
19 May 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2 + 1] annulation of para-quinone methides with bromides

Y. Su, Y. Zhao, B. Chang, Q. Ling, Y. Feng, X. Zhao, D. Huang, K. Wang, C. Huo and Y. Hu, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00778A

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