Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 54, Pages 14378-14381Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803543
Keywords
boron; C1-ammonium enolate; cooperative catalysis; Lewis bases; palladium
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Funding
- Indiana University
- NIH-NIGMS [R01GM121573]
- IU
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM121573] Funding Source: NIH RePORTER
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Cooperation between a Lewis base and Pd catalyst enables the direct enantioselective alpha-functionalization of aryl and vinyl acetic acid esters using a bifunctional B(pin)-substituted electrophile. Critical to the success of this method was the recognition that both catalysts could control the necessary stereochemical aspects; the Lewis base catalyst controls the enantioselectivity of the reaction, whereas the Pd catalyst regulates alkenyl-B(pin) configuration. This is the first example of using cooperative catalysis to control both stereochemical features during Pd-catalyzed allylic alkylation.
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