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A Double Deprotonation Strategy for Cascade Annulations of Palladium-Trimethylenemethanes and Morita-Baylis-Hillman Carbonates to Construct Bicyclo[3.1.0]hexane Frameworks. | LitMetric

A Double Deprotonation Strategy for Cascade Annulations of Palladium-Trimethylenemethanes and Morita-Baylis-Hillman Carbonates to Construct Bicyclo[3.1.0]hexane Frameworks.

Angew Chem Int Ed Engl

Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.

Published: June 2021

AI Article Synopsis

Article Abstract

Here we report that the chemoselective activation of Tsuji's 2-(cyanomethyl)allyl carbonates to generate the palladium-trimethylenemethane 1,3-dipoles via a deprotonation strategy can be realized in the presence of Morita-Baylis-Hillman carbonates from substantial activated ketones. The following S 2'-addition enables the formation of new 1,3-dipole species having an activated alkene moiety through a second deprotonation process, which then undergo cascade [1+2]/[3+2] annulations to furnish complex bicyclic [3.1.0]hexane frameworks having three contiguous quaternary stereogenic centers with good to excellent enantioselectivity. Moreover, by using benzoyl aldehyde-derived substrates, a [1+4]/[3+2] annulation sequence is similarly developed to produce fused cyclopenta[b]furan architectures.

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Source
http://dx.doi.org/10.1002/anie.202102842DOI Listing

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