期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 24, 页码 10222-10227出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja303115m
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资金
- National University of Singapore [R-143-000-469-112]
- GSK-EDB [R-143-000-491-592]
Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.
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