(4aSR,7SR,9aRS)-9a-Bromo-7-methyl-5,5-dioxo-1,2,4a,6,7,9a-hexahydro-8-oxa-5λ6-thia-1,4-benzocyclohepten-9-one

Zeller, Mat­thias; Hunter, Allen D.; Sampson, Paul; Chumachenko, Nataliya

doi:10.1107/s1600536804007603

Acta Cryst E

2004

DOI: 10.1107/s1600536804007603

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(4aSR,7SR,9aRS)-9a-Bromo-7-methyl-5,5-dioxo-1,2,4a,6,7,9a-hexahydro-8-oxa-5λ⁶-thia-1,4-benzocyclohepten-9-one

Matthias Zeller

Allen D. Hunter

Paul Sampson

et al.

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“…The relative stereochemistry of the major endo -cycloadducts 15a , b , g and minor endo -cycloadduct 16g were confirmed by their X-ray crystal structures . The relative stereochemistry of the remaining endo -cycloadducts was established by NOE experiments and 1 H NMR analysis.…”

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β-Acyloxysulfonyl Tethers for Intramolecular Diels−Alder Cycloaddition Reactions

et al. 2005

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[reaction: see text]. beta-Hydroxy sulfone-based tethers were employed for the first time to achieve thermally mediated intramolecular Diels-Alder cycloaddition. The reactions proceeded with complete regioselectivity and high (10/1) to complete endo/exo-selectivity and resulted in the preferential formation of one of the two possible endo-cycloadducts. The yields and stereoselectivities were proportional to the bulk of the R(1) substituent on the beta-acyloxysulfonyl tether.

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β-Acyloxysulfonyl Tethers for Intramolecular Diels−Alder Cycloaddition Reactions

et al. 2005

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(4aSR,7SR,9aRS)-9a-Bromo-7-methyl-5,5-dioxo-1,2,4a,6,7,9a-hexahydro-8-oxa-5λ⁶-thia-1,4-benzocyclohepten-9-one

Cited by 1 publication

References 7 publications

β-Acyloxysulfonyl Tethers for Intramolecular Diels−Alder Cycloaddition Reactions

β-Acyloxysulfonyl Tethers for Intramolecular Diels−Alder Cycloaddition Reactions

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