Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 6, Pages 1345-1355Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901465
Keywords
asymmetric catalysis; pyrrolidines; Electron-Withdrawing Group; bioimaging cell; Frontier Molecular Orbitals; BODIPY; cycloaddition
Categories
Funding
- Spanish Government [RTI2018-095038-B-I00, CTQ2016-76061-P, SAF2017-87305-R]
- Comunidad de Madrid [IND2017/IND-7809]
- European Structural and Investment Fund
- Spanish Ministry of Economy and Competitiveness, through the Maria de Maeztu'' Program of Excellence in RD [MDM-2014-0377]
- 'Severo Ochoa' Programme for Centres of Excellence in RD (MINECO) [SEV-2016-0686]
- Ministry of Economy, Industry and competitiveness of Spain [BES-2017.082521]
- CAM [2016-T2/IND-1660]
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In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines.
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