Journal
ACS CATALYSIS
Volume 8, Issue 3, Pages 1964-1972Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03744
Keywords
palladium catalysis; cyclopropanation; selectivity; enantioselectivity; (eta(3)-phenylallyl)Pd complex; DFT studies
Categories
Funding
- National Natural Science Foundation of China (NSFC) [21532010, 21472214, 21372242, 21421091, 21702109]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20030100]
- 1000-Talent Youth Plan of China
- European Community [912364]
- CSA-trust grant
- NSFC
- Research Grants Council of Hong Kong Joint Research Scheme [21361162001]
- Chinese Academy of Sciences
- Nankai University
- Technology Commission of Shanghai Municipality
- Croucher Foundation of Hong Kong
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Cyclopropanes with three chiral centers were afforded in good to high yields with dr ratio of 4-23:1 and ee of 83-99% in the reaction of acyclic amides with monosubstituted allyl carbonates as well as polyenyl carbonates under the Pd-catalysis in the presence of (S-phos,R)-SIOCPhox L1 as the ligand, while allylic alkylated products were provided only if (R-phos,R)-SIOCPhox L2 was the ligand. The amide group of product was easily reduced to hydroxymethyl group in high yield. The active reaction intermediate was determined and transition states for cyclopropanation and allylation were calculated. The origin of cyclopropane formation was investigated by experiments, NMR studies, X-ray analysis of allyl-Pd-ligand complexes, and DFT calculations.
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