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Issue 3, 2010
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Stereoselectivity in oxyallyl–furan (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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Article information


Submitted
27 Apr 2010
Accepted
17 May 2010
First published
25 Jun 2010

Chem. Sci., 2010,1, 387-392
Article type
Edge Article

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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