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Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones.

ABSTRACT: Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing ? lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.

SUBMITTER: Throup A

PROVIDER: S-EPMC5066561 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones.

Throup Adam A Patterson Laurence H LH Sheldrake Helen M HM

Organic & biomolecular chemistry 20161001 40

Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity. ...[more]

PMID: 27722445

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