doi: 10.1021/ol0067991.
Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization
Affiliations
- PMID: 11150208
- DOI: 10.1021/ol0067991
Item in Clipboard
Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization
Org Lett.
.
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.
Similar articles
-
A silicon tether approach for addition of functionalized radicals to chiral alpha-hydroxyhydrazones: diastereoselective additions of hydroxymethyl and vinyl synthons.J Org Chem. 2004 Feb 6;69(3):863-75. doi: 10.1021/jo035405r. J Org Chem. 2004. PMID: 14750816
-
Radical additions to chiral hydrazones: stereoselectivity and functional group compatibility.Top Curr Chem. 2012;320:61-91. doi: 10.1007/128_2011_163. Top Curr Chem. 2012. PMID: 21842359 Review.
-
Stereoselective quaternary center construction via atom-transfer radical cyclization using silicon tethers on acyclic precursors.Org Lett. 2009 Jul 16;11(14):3148-51. doi: 10.1021/ol901126y. Org Lett. 2009. PMID: 19552388
-
Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone.J Org Chem. 2003 Jul 11;68(14):5618-26. doi: 10.1021/jo0341057. J Org Chem. 2003. PMID: 12839454
-
Diastereoselective, titanium-mediated cyclization of omega-vinyl tethered imides.Org Lett. 2005 Dec 22;7(26):5901-4. doi: 10.1021/ol0525157. Org Lett. 2005. PMID: 16354095
Cited by
-
Control of asymmetry in the radical addition approach to chiral amine synthesis.Top Curr Chem. 2014;343:1-32. doi: 10.1007/128_2013_481. Top Curr Chem. 2014. PMID: 24085561 Free PMC article. Review.
-
Effects of alpha-Alkoxy Substitution and Conformational Constraints on 6-exo Radical Cyclizations of Hydrazones via Reversible Thiyl and Stannyl Additions.Tetrahedron. 2007 Sep 17;63(38):9373-9381. doi: 10.1016/j.tet.2007.06.117. Tetrahedron. 2007. PMID: 18797497 Free PMC article.
-
Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.Molecules. 2020 Jul 7;25(13):3094. doi: 10.3390/molecules25133094. Molecules. 2020. PMID: 32646036 Free PMC article. Review.
-
Substituent effects on the rearrangements of cyclohexyl to cyclopentyl radicals involving avermectin-related radicals.J Org Chem. 2008 Nov 7;73(21):8175-81. doi: 10.1021/jo800923a. Epub 2008 Oct 9. J Org Chem. 2008. PMID: 18842059 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
