Literature DB >> 16468714

Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans.

Roy K Bowman1, Jeffrey S Johnson.   

Abstract

[reaction: see text] Mild Ni(0)-catalyzed rearrangements of 1-acyl-2-vinylcyclopropanes have been developed. The room-temperature isomerizations afford dihydrofuran products in yields regularly greater than 90%. A highly substituted, stereochemically defined cyclopropane was employed in the rearrangement to evaluate the reaction mechanism. Product analysis indicates that the overall reaction proceeds with retention of configuration at the vinyl-bearing stereogenic center.

Entities:  

Year:  2006        PMID： 16468714     DOI： 10.1021/ol052700k

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


  8 in total

1.  Polarity inversion of donor-acceptor cyclopropanes: disubstituted δ-lactones via enantioselective iridium catalysis.

Authors:  Joseph Moran; Austin G Smith; Ryan M Carris; Jeffrey S Johnson; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-10-31       Impact factor: 15.419

2.  A facile metal-free one-flask synthesis of multi-substituted furans via a BF3·Et2O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones.

Authors:  Zixin Zhang; Aimin Huang; Lin Ma; Jian-Hua Xu; Min Zhang
Journal:  RSC Adv       Date:  2022-05-18       Impact factor: 4.036

3.  Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Authors:  Barry M Trost; Patrick J Morris; Simon J Sprague
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

4.  Nickel-catalyzed reactions of vinyl aziridines and aziridinylen-ynes.

Authors:  Gang Zuo; Kainan Zhang; Janis Louie
Journal:  Tetrahedron Lett       Date:  2008-11-24       Impact factor: 2.415

5.  Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

Authors:  André U Augustin; Peter G Jones; Daniel B Werz
Journal:  Chemistry       Date:  2019-08-07       Impact factor: 5.236

6.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087

7.  Non-decarbonylative photochemical versus thermal activation of Bu4N[Fe(CO)3(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes.

Authors:  Che-Hung Lin; Dominik Pursley; Johannes E M N Klein; Johannes Teske; Jennifer A Allen; Fabian Rami; Andreas Köhn; Bernd Plietker
Journal:  Chem Sci       Date:  2015-09-03       Impact factor: 9.825

8.  Synthesis and Pharmacological Evaluation of Triazolopyrimidinone Derivatives as Noncompetitive, Intracellular Antagonists for CC Chemokine Receptors 2 and 5.

Authors:  Natalia V Ortiz Zacarías; Jacobus P D van Veldhoven; Lisa S den Hollander; Burak Dogan; Joseph Openy; Ya-Yun Hsiao; Eelke B Lenselink; Laura H Heitman; Adriaan P IJzerman
Journal:  J Med Chem       Date:  2019-12-13       Impact factor: 7.446
  8 in total

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