2403-57-8Relevant articles and documents
Rapid Fluorescent Screening for Bifunctional Amine-Acid Catalysts: Efficient Syntheses of Quaternary Carbon-Containing Aldols under Organocatalysis
Mase, Nobuyuki,Tanaka, Fujie,Barbas III, Carlos F.
, p. 4369 - 4372 (2003)
(Equation presented) Direct catalytic aldol reactions of α.α-dialkylaldehyde donors and arylaldehyde acceptors have been performed using pyrrolidine-acetic acid bifunctional catalysts. This general and practical amine-acid combination was identified by sc
Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α-Branched Ketones
Liu, Yong-Peng,Wang, Shu-Ren,Chen, Ting-Ting,Yu, Cun-Cun,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 971 - 975 (2019/01/25)
A direct transformation of secondary amides into α-branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot coupling of secondary amides with aldehydes to yield ketones. (Figure presented.).
Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis
Chen, Xiaobei,Fan, Huaqiang,Zhang, Shilei,Yu, Chenguang,Wang, Wei
supporting information, p. 716 - 723 (2016/01/12)
An unprecedented tandem N-alkylation-ionic aza-Cope (or Claisen) rearrangement-hydrolysis reaction of readily available indolyl bromides with enamines is described. Due to the complicated nature of the two processes, an operationally simple N-alkylation and subsequent microwave-irradiated ionic aza-Cope rearrangement-hydrolysis process has been uncovered. The tandem reaction serves as a powerful approach to the preparation of synthetically and biologically important, but challenging, 2-reverse quaternary-centered prenylated indoles with high efficiency. Notably, unusual nonaromatic 3-methylene-2,3-dihydro-1H-indole architectures, instead of aromatic indoles, are produced. Furthermore, the aza-Cope rearrangement reaction proceeds highly regioselectively to give the quaternary-centered reverse prenyl functionality, which often produces a mixture of two regioisomers by reported methods. The synthetic value of the resulting nonaromatic 3-methylene-2,3-dihydro-1Hindole architectures has been demonstrated as versatile building blocks in the efficient synthesis of structurally diverse 2-reverse prenylated indoles, such as indolines, indolefused sultams and lactams, and the natural product bruceolline D.