Trimethylenemethane cycloaddition is the formal (3+2) annulation of trimethylenemethane (TMM) derivatives to two-atom pi systems. Although TMM itself is too reactive and unstable to be stored, reagents which can generate TMM or TMM synthons in situ can be used to effect cycloaddition reactions with appropriate electron acceptors .

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In summary, we have developed conditions to effect an asymmetric palladium-catalyzed [3+2] cycloaddition reaction between in situ generated Pd-TMM intermediates and various olefins, in spite of the large distance between the chiral ligands and the asymmetric bond-forming event.

We have developed a successful catalytic, asymmetric [3+2] TMM cycloaddition reaction with imine acceptors that affords pyrrolidine products. The methodology described herein showcases the enantioselective addition of a carbon nucleophile to an imine.

Apr 15, 2004 · The reaction serves well for the [3 + 2] cycloaddition to electron-deficient acceptors, and it has been applied to the synthesis of several cyclopentanoid natural products. This review surveys the [3 + 2] cycloaddition reactions of …

The synthesis of marcfortine B (8) began with palladium-catalyzed intermolecular carboxylatve TMM [3 + 2] cycloaddition of enone 65 and TMM donor 62 to forge the highly-substituted spirocyclic cyclopentane 66a .

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Dec 7, 2011 · The conditions developed to effect an asymmetric TMM reaction using 2-trimethylsilylmethyl allyl acetate were shown to be tolerant of a wide variety of alkene acceptors, providing the desired methylenecyclopentanes with high levels of enantioselectivity.

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Trimethylenemethane (often abbreviated TMM) is a chemical compound with formula C 4 H 6. It is a neutral free molecule with two unsatisfied valence bonds, and is therefore a highly reactive free radical. Formally, it can be viewed as an isobutylene molecule C 4 H 8 with two hydrogen atoms removed from the terminal methyl groups.