Journal
ACS CATALYSIS
Volume 8, Issue 11, Pages 10537-10544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b03507
Keywords
cooperative catalysis; Lewis base; palladium; allylic alkylation; enantioselective; synergistic
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Funding
- Indiana University
- NIH [R01GM121573]
- IU Vice Provost for Research through the Research Equipment Fund
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM121573] Funding Source: NIH RePORTER
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We have identified a generally effective Pd catalyst for the highly enantioselective cooperative Lewis base/Pd-catalyzed alpha-allylation of aryl acetic esters using electron-deficient electrophiles. Changing between aldehyde, ketone, ester, and amide substituents at the terminus of intermediate cationic pi-(allyl)Pd species affects both the efficiency of the reaction and, in the case of amides, control over the stereochemistry of the product alkene, as a function of the ligand. Tris[tri(2-thienyl)phosphino]Pd(0) serves as a broadly effective catalyst and overcomes these challenges to provide a general, high-yielding, and operationally simple C(sp(3))-C(sp(3)) bond-forming method that gives products with high levels of enantioselectivity.
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