Literature DB >> 24606195

Lewis acid catalyzed (3 + 2)-annulations of donor-acceptor cyclopropanes and ynamides.

William D Mackay1, Meryem Fistikci, Ryan M Carris, Jeffrey S Johnson.   

Abstract

The Sc(OTf)3-catalyzed (3 + 2)-annulation of donor-acceptor cyclopropanes and ynamides is described, providing the corresponding cyclopentene sulfonamides in good to excellent yield. Deprotection and hydrolysis of the resulting ensulfonamides delivers 2,3-substituted cyclopentanones with high diastereoselectivity.

Entities:  

Year:  2014        PMID： 24606195     DOI： 10.1021/ol500256n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Three-Dimensional Large-Scale Fused Silica Microfluidic Chips Enabled by Hybrid Laser Microfabrication for Continuous-Flow UV Photochemical Synthesis.

Authors:  Aodong Zhang; Jian Xu; Yucen Li; Ming Hu; Zijie Lin; Yunpeng Song; Jia Qi; Wei Chen; Zhaoxiang Liu; Ya Cheng
Journal:  Micromachines (Basel)       Date:  2022-03-30       Impact factor: 3.523

2.  Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides.

Authors:  Dongxin Zhang; Jingjing Man; Yan Chen; Lei Yin; Junchao Zhong; Qian-Feng Zhang
Journal:  RSC Adv       Date:  2019-04-25       Impact factor: 4.036

3.  Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

Authors:  Johannes Preindl; Shyamal Chakrabarty; Jérôme Waser
Journal:  Chem Sci       Date:  2017-08-25       Impact factor: 9.825

4.  Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.

Authors:  Ivan A Andreev; Nina K Ratmanova; André U Augustin; Olga A Ivanova; Irina I Levina; Victor N Khrustalev; Daniel B Werz; Igor V Trushkov
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

5.  Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines.

Authors:  Gwyndaf A Oliver; Maximilian N Loch; André U Augustin; Pit Steinbach; Mohammed Sharique; Uttam K Tambar; Peter G Jones; Christoph Bannwarth; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-29       Impact factor: 16.823
  5 in total

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