Literature DB >> 12837080

Formal [3 + 2] cycloadditions of donor-acceptor cyclopropanes and nitriles.

Ming Yu1, Brian L Pagenkopf.   

Abstract

Donor-acceptor cyclopropanes activated with Me3SiOTf cleave to reactive intermediates that can be efficiently intercepted by nitriles in a formal [3 + 2] dipolar cycloaddition reaction. Aliphatic, aromatic, and alpha,beta-unsaturated nitriles are excellent reaction partners, giving synthetically useful 2H-3,4-dihydropyrrole cycloaddition products in high yield.

Entities:  

Year:  2003        PMID： 12837080     DOI： 10.1021/ja029716f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  3 in total

1.  Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Authors:  John R Goodell; Jennifer L Poole; Aaron B Beeler; Jeffrey Aubé; John A Porco
Journal:  J Org Chem       Date:  2011-11-01       Impact factor: 4.354

2.  Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives.

Authors:  Murugesan Thangamani; Subaramaniam Thangamalar; Kannupal Srinivasan
Journal:  RSC Adv       Date:  2021-04-21       Impact factor: 3.361

3.  Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes.

Authors:  Amanda Bunyamin; Carol Hua; Anastasios Polyzos; Daniel L Priebbenow
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825
  3 in total

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