doi: 10.1021/ol702115h.
Epub 2007 Oct 13.
Iridium(I)-catalyzed stereospecific decarboxylative allylic amidation of chiral branched benzyl allyl imidodicarboxylates
Affiliations
- PMID: 17935343
- DOI: 10.1021/ol702115h
Item in Clipboard
Iridium(I)-catalyzed stereospecific decarboxylative allylic amidation of chiral branched benzyl allyl imidodicarboxylates
Org Lett.
.
Abstract
Ir(I)-catalyzed decarboxylative allylic amidation of chiral branched benzyl allyl imidodicarboxylates has been shown to proceed with complete retention of enantiomeric purity and configuration. The transformation is stereospecific and appears to be quite general, accommodating a wide range of R groups.
Similar articles
-
Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products.J Am Chem Soc. 2006 Sep 13;128(36):11770-1. doi: 10.1021/ja0644273. J Am Chem Soc. 2006. PMID: 16953612
-
Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids.J Org Chem. 2011 Jul 1;76(13):5495-501. doi: 10.1021/jo200720c. Epub 2011 Jun 8. J Org Chem. 2011. PMID: 21563816
-
Iridium(I)-catalyzed regio- and enantioselective decarboxylative allylic amidation of substituted allyl benzyl imidodicarbonates.J Am Chem Soc. 2007 Jan 31;129(4):774-5. doi: 10.1021/ja067966g. J Am Chem Soc. 2007. PMID: 17243809 No abstract available.
-
Recent advances and applications of iridium-catalysed asymmetric allylic substitution.Org Biomol Chem. 2012 Apr 28;10(16):3147-63. doi: 10.1039/c2ob07086c. Epub 2012 Mar 12. Org Biomol Chem. 2012. PMID: 22407450 Review.
-
Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions.Chem Rev. 2008 Aug;108(8):2796-823. doi: 10.1021/cr0683515. Epub 2008 Aug 1. Chem Rev. 2008. PMID: 18671436 Review. No abstract available.
Cited by
-
Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals.Org Lett. 2020 Jun 5;22(11):4113-4117. doi: 10.1021/acs.orglett.0c01166. Epub 2020 May 11. Org Lett. 2020. PMID: 32392075 Free PMC article.
-
Origins of Regioselectivity in Iridium Catalyzed Allylic Substitution.J Am Chem Soc. 2015 Dec 2;137(47):14968-81. doi: 10.1021/jacs.5b08911. Epub 2015 Nov 20. J Am Chem Soc. 2015. PMID: 26498382 Free PMC article.
-
Transition metal-catalyzed decarboxylative allylation and benzylation reactions.Chem Rev. 2011 Mar 9;111(3):1846-913. doi: 10.1021/cr1002744. Epub 2011 Jan 14. Chem Rev. 2011. PMID: 21235271 Free PMC article. Review.
-
Direct, intermolecular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines.Org Lett. 2009 Jul 2;11(13):2944-7. doi: 10.1021/ol901151u. Org Lett. 2009. PMID: 19552468 Free PMC article.
-
Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.ACS Med Chem Lett. 2011 Mar 4;2(5):348-52. doi: 10.1021/ml100287y. eCollection 2011 May 12. ACS Med Chem Lett. 2011. PMID: 24900316 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
