doi: 10.1021/ja054109o.
Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation
Affiliations
- PMID: 16448093
- DOI: 10.1021/ja054109o
Item in Clipboard
Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation
J Am Chem Soc.
.
Abstract
A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%).
Similar articles
-
Highly enantioselective synthesis of tetrahydrocarbolines via iridium-catalyzed intramolecular Friedel-Crafts type allylic alkylation reactions.Org Lett. 2013 Dec 6;15(23):5909-11. doi: 10.1021/ol4027717. Epub 2013 Nov 11. Org Lett. 2013. PMID: 24215126
-
Catalytic asymmetric total synthesis of tangutorine.Org Lett. 2010 Feb 19;12(4):872-5. doi: 10.1021/ol902929a. Org Lett. 2010. PMID: 20092264
-
Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications.J Am Chem Soc. 2004 Sep 29;126(38):11966-83. doi: 10.1021/ja048078t. J Am Chem Soc. 2004. PMID: 15382932
-
Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool.Chem Pharm Bull (Tokyo). 2002 Jan;50(1):1-14. doi: 10.1248/cpb.50.1. Chem Pharm Bull (Tokyo). 2002. PMID: 11824567 Review.
-
Annulative Allylic Alkylation Reactions between Dual Electrophiles and Dual Nucleophiles: Applications in Complex Molecule Synthesis.Chemistry. 2020 Feb 11;26(9):1906-1921. doi: 10.1002/chem.201903961. Epub 2019 Dec 19. Chemistry. 2020. PMID: 31693220 Review.
Cited by
-
Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes.Beilstein J Org Chem. 2012;8:1730-46. doi: 10.3762/bjoc.8.198. Epub 2012 Oct 11. Beilstein J Org Chem. 2012. PMID: 23209507 Free PMC article.
-
Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.Org Lett. 2011 Oct 21;13(20):5564-7. doi: 10.1021/ol202300t. Epub 2011 Sep 15. Org Lett. 2011. PMID: 21919478 Free PMC article.
-
Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.Angew Chem Int Ed Engl. 2020 May 4;59(19):7598-7604. doi: 10.1002/anie.202001956. Epub 2020 Mar 11. Angew Chem Int Ed Engl. 2020. PMID: 32091146 Free PMC article.
-
Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate.Org Lett. 2014 Jul 3;16(13):3480-3. doi: 10.1021/ol501409a. Epub 2014 Jun 25. Org Lett. 2014. PMID: 24964382 Free PMC article.
-
Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.Org Lett. 2013 Mar 1;15(5):1140-3. doi: 10.1021/ol400334u. Epub 2013 Feb 21. Org Lett. 2013. PMID: 23427905 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
