Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 14, Pages 4334-4337Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411593
Keywords
asymmetric catalysis; cations; crown compounds; host-guest systems; hydrogenation
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Funding
- National Basic Research Program of China (973 Program) [2011CB808600]
- National Natural Science Foundation of China [21232008, 21373231]
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An aza-crown ether, modified phosphoramidite ligand, has been designed and synthesized. The ON/OFF reversible switch of catalytic activity for its rhodium catalyst was thoroughly investigated in the asymmetric hydrogenation of dehydroamino acid esters modulated by host-guest interactions. In the OFF state, the catalyst is almost inactive (less than 1% conversion) because of the formation of an intermolecular sandwich complex by two aza-crown ether moities and the cationic rhodium metal center. In using alkali-metal-cations as the trigger, the catalytic activity was turned ON and consequently resulted in full conversions and excellent enantioselectivities (up to 98% ee).
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