期刊
ORGANIC LETTERS
卷 13, 期 20, 页码 5420-5423出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol201730q
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-
资金
- NIH [R01GM071779, P41GM081282]
General base-catalyzed double-Michael reactions of allenes with various dinucleophiles are described. The reactions are facilitated most efficiently by a catalytic amount of trimethylphosphIne, affording six types of C2-functionalized benzannulated five-membered heterocycles: benzimidazolines, benzoxazolines, benzothiazolines, 1,3-benzodioxoles, 1,3-benzoxathioles, and 1,3-benzodithioles. This atom-economical reaction Is operationally simple and provides the product heterocycles in good to excellent yields. Careful mechanistic studies unveiled the phosphine-triggered general base catalysis pathway. Furthermore, the double-Michael reaction can serve as an alternative method for the selective monoketalization of beta-diketones.
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