Access to Complex Scaffolds Through [2 + 2] Cycloadditions of Strained Cyclic Allenes

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2024 May 20

PMID 38768558

Authors

Matthew S McVeigh

Jacob P Sorrentino

Allison T Hands

Neil K Garg

Affiliations

Soon will be listed here.

Abstract

We report the strain-induced [2 + 2] cycloadditions of cyclic allenes for the assembly of highly substituted cyclobutanes. By judicious choice of trapping agent, complex scaffolds bearing heteroatoms, fused rings, contiguous stereocenters, spirocycles, and quaternary centers are ultimately accessible. Moreover, we show that the resulting cycloadducts can undergo thermal isomerization. This study provides an alternative strategy to photochemical [2 + 2] cycloadditions for accessing highly functionalized cyclobutanes, while validating the use of underexplored strained intermediates for the assembly of complex architectures.

Citing Articles

Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.

Wonilowicz L, Mehta M, Kamecke L, French S, Garg N Org Lett. 2024; 26(30):6465-6470.

PMID: 39046907 PMC: 11459240. DOI: 10.1021/acs.orglett.4c02294.

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