期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 4, 页码 1632-1636出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404327
关键词
asymmetric catalysis; C-H functionalization; hydride shift; scandium; spirooxindoles
资金
- National Natural Science Foundation of China [21290182, 21321061, 21172151]
- Ministry of Education [NCET-11-0345]
- National Basic Research Program of China (973 Program) [2011CB808600]
The direct functionalization of sp(3) C-H bonds through a tandem 1,5-hydride shift/ring closure is described. Various optically active spirooxindole tetrahydroquinoline derivatives bearing contiguous quaternary or tertiary stereogenic carbon centers were readily synthesized. A chiral scandium complex of N,N'-dioxide promoted the reactions in good yields (up to 97%) with excellent diastereoselectivities (>20:1) and enantioselectivities (up to 94% ee). Kinetic isotope effect (KIE) experiments and internal redox reactions of chiral substrates were conducted, and the results provided intriguing information that helped clarify the mechanism of the reaction.
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