期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 37, 页码 12102-12105出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806742
关键词
benzylation; cooperative catalysis; enantioselectivity; Lewis bases; palladium
资金
- Indiana University
- National Institutes of Health [R01GM121573]
- IU Vice Provost for Research through the Research Equipment Fund
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM121573] Funding Source: NIH RePORTER
The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.
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