Asymmetric Organocatalysis Combined with Palladium Catalysis: Synergistic Effect on Enantioselective Mannich/α-Allylation Sequential Reactions of Pyrazolones in Constructing Vicinal Quaternary Stereocenters.

Clicks: 416
ID: 64658
2019
Article Quality & Performance Metrics
Overall Quality
Not rated
Combines reader engagement with the AI quality analysis. This article has not been analysed, so there is no overall score — reader engagement is measured and shown alongside.
AI Quality Assessment
Not analyzed
Readership in this journal
Emerging

Ranked #21 of 145 articles by views in Organic letters

Most read Least read

Bar heights use a square-root scale. Only the 120 most-read articles are drawn; the journal has 145 in total.

Mint this article as an NFT
Not yet minted

Create a permanent, verifiable on-chain record of this article on the Scimatic Network. The NFT is held in your Journament account, and you can withdraw it to your own wallet at any time.

5 SUSD one-off · no wallet required
Sign in to mint
Abstract
In this letter, an efficient one-pot asymmetric sequential reaction is achieved by organo/transition metal relay catalysis in constructing two consecutive C-C bonds, which involves enantioselective amino squaramide catalytic Mannich-type addition of pyrazolones to isatin-derived ketimines and a subsequent palladium catalyzed diastereoselective allylic alkylation of pyrazolones with allylic acetates. An array of novel pyrazolone-aminooxindole-propylene structural motifs are obtained in a high level of yield and with excellent enantio- and diastereoselectivity (up to 95% yield, >20:1 dr, >99% ee). This methodology features the formation of vicinal quarternary carbon-stereocenters, and the second all-carbon tetrasubstituted stereogenic center is induced by joint action of the achiral palladium catalysis and the chiral environment generated from the Mannich step. Moreover, the usefulness of this methodology is highlighted by converting the allylic product into the carbonyl compound.
Reference Key
wu2019asymmetricorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Wu, Gengxin;Xu, Haohan;Liu, Ziran;Liu, Yonghong;Yang, Xiang;Zhang, Xulong;Huang, Yan;
Journal Organic letters
Year 2019
DOI
10.1021/acs.orglett.9b02440
URL
Keywords
uplc-ms/ms monosaccharide composition polyporus umbellatus polysaccharide pre-column derivation

Citations

No citations found. To add a citation, contact the admin at info@scimatic.org

Comments

No comments yet. Be the first to comment on this article.