Literature DB >> 11150208

Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization

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Abstract

A diastereoselective method for addition of a vinyl group to alpha-hydroxy hydrazones under neutral tin-free radical cyclization conditions, leading to substituted vinylglycinols, is presented. Tandem thiyl radical addition/cyclization upon a silicon-tethered vinyl group followed by treatment with potassium fluoride accomplishes a one-pot neutral vinyl addition process to afford acyclic allylic anti-hydrazino alcohols in good yield.

Entities:  

Year:  2000        PMID： 11150208     DOI： 10.1021/ol0067991

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


  4 in total

1.  Effects of alpha-Alkoxy Substitution and Conformational Constraints on 6-exo Radical Cyclizations of Hydrazones via Reversible Thiyl and Stannyl Additions.

Authors:  Gregory K Friestad; Alex K Mathies
Journal:  Tetrahedron       Date:  2007-09-17       Impact factor: 2.457

2.  Substituent effects on the rearrangements of cyclohexyl to cyclopentyl radicals involving avermectin-related radicals.

Authors:  Jennifer A R Luft; Tammo Winkler; Fiona M Kessabi; K N Houk
Journal:  J Org Chem       Date:  2008-10-09       Impact factor: 4.354

Review 3.  Control of asymmetry in the radical addition approach to chiral amine synthesis.

Authors:  Gregory K Friestad
Journal:  Top Curr Chem       Date:  2014

Review 4.  Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.

Authors:  Dylan M Lynch; Eoin M Scanlan
Journal:  Molecules       Date:  2020-07-07       Impact factor: 4.411
  4 in total

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