Literature DB >> 11463299

Intramolecular aminyl and iminyl radical additions to alpha,beta-unsaturated esters. Diastereoselective tandem cyclofunctionalization and hydrogen transfer reactions.

Y Guindon1, B Guérin, S R Landry.   

Abstract

[reaction: see text] A tandem process featuring intramolecular aminyl radical cyclofunctionalization and hydrogen transfer affords 2,3-trans-disubstituted pyrrolidines with anti or syn diastereoselectivity. The extension of this strategy to iminyl radicals gives trans-anti pyrrolenines with high levels of 1,2-induction in both steps of the tandem process.

Entities:  

Year:  2001        PMID： 11463299     DOI： 10.1021/ol0160809

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


  5 in total

1.  Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations.

Authors:  Jennifer L Stockdill; Alberto M Lopez; Ahmad A Ibrahim
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

Authors:  Robert M Demoret; Meghan A Baker; Masaki Ohtawa; Shuming Chen; Ching Ching Lam; Sophia Khom; Marisa Roberto; Stefano Forli; Kendall N Houk; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

3.  Rapid access to the heterocyclic core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids via tandem cyclization of a neutral aminyl radical.

Authors:  Ahmad A Ibrahim; Alexander N Golonka; Alberto M Lopez; Jennifer L Stockdill
Journal:  Org Lett       Date:  2014-02-07       Impact factor: 6.005

4.  Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions.

Authors:  Jacob Davies; Samuel G Booth; Stephanie Essafi; Robert A W Dryfe; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-28       Impact factor: 15.336

Review 5.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  5 in total

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