- Preparation of 4-(Nitromethyl)furan Derivatives and Their Application in the Syntheses of Bis(furan-2-yl)oximes
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An efficient method for the preparation of tetrasubstituted furans, which contains a nitromethyl group at the 4-position, has been developed. The applications of 4-(nitromethyl)furans on the synthesis of highly functionalized bis(furyl)oxime were explored
- Wan, Yinbo,Zhu, Yang,Peng, Haiyun,Deng, Guisheng
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p. 281 - 293
(2021/12/27)
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- Mutually complementary metal- and organocatalysis with collective synthesis: Asymmetric conjugate addition of 1,3-carbonyl compounds to nitroenynes and further reactions of the products
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The first metal-catalyzed 1,4-selective asymmetric addition of malonates to nitroenynes promoted by a simple chiral nickel(II)-diamine catalyst, was developed, facilitating a mild synthesis of a novel type of multifunctional chiral b-alkynyl acids bearing a nitro group. Based on this protocol, we have developed a practical and collective synthesis of a series of diverse functional molecules and building blocks including new types of chiral balkynyl- γ-amino acids, b-functionalized chiral dketo- γ-lactones, chiral g-alkylidenelactones, alkynylsubstituted pyrrole-3-carboxylic acid derivatives, tetrasubstituted furans and chiral b-alkynyl-γ-lactams. Notably, we discovered two unusual tandem reactions leading to functionalized chiral 1,5-dicarbonyl compounds. In addition, by employing simple bifunctional organocatalysts, we have developed the first regio-, diastereo- and enantioselective conjugate addition of a-substituted b-keto esters to nitroenynes, which is poorly diastereoselective with chiral nickel(II)-diamine catalysts, providing a new entry to adjacent quaternary and tertiary stereocenters in one step. Based on this protocol, we have developed a concise asymmetric synthesis of conformationally constrained bicyclic γ2-amino acids featuring an alkynyl side chain with an adjacent quaternary carbon stereocenter. The study described here demonstrates that the mutually complementary strategy of transition metal catalysis and organocatalysis is a powerful and promising tool in catalytic asymmetric synthesis.
- Li, Xiang,Li, Xiaojiao,Peng, Fangzhi,Shao, Zhihui
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p. 2873 - 2885
(2013/01/15)
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