A facile method for the synthesis of highly substituted six-membered rings: Mukaiyama-Aldol-Prins cascade reaction
- PMID: 20481623
- DOI: 10.1021/ol100937r
A facile method for the synthesis of highly substituted six-membered rings: Mukaiyama-Aldol-Prins cascade reaction
Abstract
A highly efficient cascade reaction has been developed using cheap commercially available or easily accessible starting materials. It has the ability to construct highly functionalized six-membered ring with three to four stereogenic centers in high yields.
Similar articles
-
Control of up to five stereocenters in a cascade reaction: synthesis of highly functionalized five-membered rings.J Am Chem Soc. 2008 Jun 11;130(23):7194-5. doi: 10.1021/ja801488z. Epub 2008 May 20. J Am Chem Soc. 2008. PMID: 18489092
-
Titanium(IV)-promoted Mukaiyama aldol-Prins cyclizations.Org Lett. 2003 Aug 21;5(17):3163-6. doi: 10.1021/ol035303n. Org Lett. 2003. PMID: 12917007
-
A facile synthesis of highly substituted five-membered rings: Mukaiyama-aldol-oxonoium-ene (MAOE) domino reaction.Chem Asian J. 2011 Aug 1;6(8):1948-51. doi: 10.1002/asia.201000884. Epub 2011 May 6. Chem Asian J. 2011. PMID: 21557483 No abstract available.
-
Synthetic studies on the MARDi cascade: stereoselective synthesis of heterocyclic seven-membered rings.Org Lett. 2006 Oct 12;8(21):4819-22. doi: 10.1021/ol061874e. Org Lett. 2006. PMID: 17020311
-
Stereoselective construction of seven-membered rings with an all-carbon quaternary center by direct Tiffeneau-Demjanov-type ring expansion.J Am Chem Soc. 2009 May 13;131(18):6614-7. doi: 10.1021/ja900941k. J Am Chem Soc. 2009. PMID: 19378970
Cited by
-
Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.J Org Chem. 2011 Nov 18;76(22):9269-77. doi: 10.1021/jo201478d. Epub 2011 Oct 25. J Org Chem. 2011. PMID: 21916500 Free PMC article.
-
Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.Org Lett. 2013 Aug 16;15(16):4070-3. doi: 10.1021/ol401600j. Epub 2013 Aug 1. Org Lett. 2013. PMID: 23901903 Free PMC article.
-
Stereocontrolled and time-honored access to piperidine- and pyrrolidine-fused 3-methylenetetrahydropyrans using lactam-tethered alkenols.RSC Adv. 2024 Aug 27;14(37):26913-26919. doi: 10.1039/d4ra04916k. eCollection 2024 Aug 22. RSC Adv. 2024. PMID: 39193285 Free PMC article.
LinkOut - more resources
Full Text Sources