期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 359, 期 1, 页码 49-57出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600954
关键词
[3+2] annulation.; difluoromethylthiolation; Morita-Baylis-Hillman (MBH) carbonates; organocatalysis; spirocyclic oxindoles
资金
- National Basic Research Program of China [(973)] [2015CB856603]
- National Natural Science Foundation of China [20472096, 21372241, 21361140350, 20672127, 21421091, 21372250, 21121062, 21302203, 20732008, 21572052]
In this paper, we report that a novel tertiary amine-catalyzed [3+2] annulation between Morita-Baylis-Hillman (MBH) carbonates derived from isatins with thiocarbonyl fluoride (F2C=S) in situ generated from Zard's reagent proceeds smoothly under mild conditions, affording difluoro-methylthiolated spirocyclic oxindoles in good to excellent yields. Moreover, the asymmetric variant could be realized with a modified Cinchona alkaloid, giving the desired cyclic adducts in good to excellent yields with good enantioselectivities.
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