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Issue 3, 2010
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Stereoselectivity in oxyallylfuran (4 + 3) cycloadditions: control of intermediate conformations and dispersive stabilisation in cycloadditions involving oxazolidinone auxiliaries

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Abstract

Chiral oxazolidinones were previously thought to control cycloaddition stereoselectivity by steric crowding of one face of the substrate. We have discovered that in (4 + 3) cycloaddition reactions of oxyallyls, the stereoinduction is caused instead by stabilising CH–π interactions that lead to reaction at the more crowded face of the oxyallyl. Density functional theory calculations on the (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls with furans establish unexpected transition state conformations and a new explanation of selectivity.

Graphical abstract: Stereoselectivity in oxyallyl–furan (4 + 3) cycloadditions: control of intermediate conformations and dispersive stabilisation in cycloadditions involving oxazolidinone auxiliaries

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Publication details

The article was received on 27 Apr 2010, accepted on 17 May 2010 and first published on 25 Jun 2010


Article type: Edge Article
DOI: 10.1039/C0SC00280A
Citation: Chem. Sci., 2010,1, 387-392
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    Stereoselectivity in oxyallylfuran (4 + 3) cycloadditions: control of intermediate conformations and dispersive stabilisation in cycloadditions involving oxazolidinone auxiliaries

    E. H. Krenske, K. N. Houk, A. G. Lohse, J. E. Antoline and R. P. Hsung, Chem. Sci., 2010, 1, 387
    DOI: 10.1039/C0SC00280A

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