Journal
CHEMICAL SCIENCE
Volume 1, Issue 3, Pages 387-392Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00280a
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- NIH
- NSF
- Australian-American Fulbright Commission [GM-36700, GM66055]
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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-pi 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.
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