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Develop a catalytic [4 + 2]-annulation protocol using aminocyclobutanes and aldehydes or enol ethers to synthesize tetrahydropyranyl amines, nucleoside analogues, and cyclohexylamines.

February 4, 2015Organic LettersOpen Access

[4 + 2]-Annulations of Aminocyclobutanes

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Develop a catalytic [4 + 2]-annulation protocol using aminocyclobutanes and aldehydes or enol ethers to synthesize tetrahydropyranyl amines, nucleoside analogues, and cyclohexylamines.
Coupled phthalimido cyclobutane dicarboxylates with aromatic aldehydes using Lewis acid catalysts, specifically scandium triflate or iron trichloride.
Expanded substrate scope using thymine- and fluorouracil-substituted cyclobutanes, as well as enol ethers, to form diverse six-membered ring scaffolds.
Obtained tetrahydropyranyl amines in 53% to 92% yield with diastereomeric ratios ranging from 3:1 to 17:1.
Achieved direct access to six-membered nucleoside analogues using thymine- or fluorouracil-functionalized cyclobutanes.
Delivered corresponding cyclohexylamines through the [4 + 2]-annulation of aminocyclobutanes with enol ethers.

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Implication

Synthetic study demonstrates [4 + 2]-annulations of aminocyclobutanes with aldehydes, highlighting direct synthesis of tetrahydropyranyl amines and six-membered nucleoside analogues.

Cite This Study

Perrotta et al. (2015) studied this question.

synapsesocial.com/papers/6a9b2a4cb71c716290fcf40c https://doi.org/10.1021/acs.orglett.5b00149

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Implication

Synthetic study demonstrates [4 + 2]-annulations of aminocyclobutanes with aldehydes, highlighting direct synthesis of tetrahydropyranyl amines and six-membered nucleoside analogues.

[4 + 2]-Annulations of Aminocyclobutanes

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Implication

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[4 + 2]-Annulations of Aminocyclobutanes

Key Points

Discussion

Implication

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