Journal
SCIENCE
Volume 327, Issue 5968, Pages 986-990Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1182826
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Funding
- NIH [GM-43214, P50 GM-69721]
- Dreyfus Foundation
- American Chemical Society
- Roche
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Cationic organic intermediates participate in a wide variety of useful synthetic transformations, but their high reactivity can render selectivity in competing pathways difficult to control. Here, we describe a strategy for inducing enantioselectivity in reactions of protio-iminium ions, wherein a chiral catalyst interacts with the highly reactive intermediate through a network of noncovalent interactions. This interaction leads to an attenuation of the reactivity of the iminium ion and allows high enantioselectivity in cycloadditions with electron-rich alkenes (the Povarov reaction). A detailed experimental and computational analysis of this catalyst system has revealed the precise nature of the catalyst-substrate interactions and the likely basis for enantioinduction.
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