期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 10, 页码 5546-5557出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00567
关键词
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资金
- Spanish MINECO [FEDER-CTQ2014-59870-P]
- JC y L [FEDER-VA115P17]
Novel styryl-substituted thioureas and squaramides were obtained in three steps from commercially available 4-hydroxy-3,5-dichloroaniline. These organocatalysts promote cascade reactions in high yields and excellent stereoselection. By using only a 5 mol % loading of catalyst, it is possible to obtain 2,3,4-trisubstituted benzopyrans by reaction of alpha-amido sulfones derived from salicyladehydes and nitrostyrenes or 2,3,4-trisubstituted 4H-chromenes by reaction of the same alpha-amido sulfones with (phenylsulfonyl)acetonitrile in excellent diastereo- and enantioselectivities. Two polymeric thioureas and squaramides were prepared by copolymerization of the best monomeric catalysts with styrene and divinylbenzene and used for the same transformations. These polymers behave also as excellent stereoselective catalysts that can be recovered and reused for five cycles.
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