Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 6, Pages 1749-1751Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b00303
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- ERC
- EPSRC
- EU
- EPSRC [EP/H021620/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H021620/2] Funding Source: researchfish
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Mechanical point-chirality in a [2]rotaxane is utilized for asymmetric catalysis. Stable enantiomers of the rotaxane result from a bulky group in the middle of the thread preventing a benzylic amide macrocycle shuttling between different sides of a prochiral center, creating point chirality in the vicinity of a secondary amine group. The resulting mechanochirogenesis delivers enantioselective organocatalysis via both enamine (up to 71:29 er) and iminium (up to 68:32 er) activation modes.
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