doi: 10.1021/ol9028258.
Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines
Affiliations
- PMID: 20099813
- DOI: 10.1021/ol9028258
Item in Clipboard
Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines
Org Lett.
.
Abstract
A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.
Similar articles
-
Indium-mediated asymmetric intramolecular allenylation of N-tert-butanesulfinyl imines: efficient and practical access to chiral 3-allenyl-4-aminochromanes.Org Lett. 2014 Aug 15;16(16):4118-21. doi: 10.1021/ol501815e. Epub 2014 Jul 28. Org Lett. 2014. PMID: 25068528
-
Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines.Org Lett. 2013 Apr 5;15(7):1658-61. doi: 10.1021/ol400439g. Epub 2013 Mar 13. Org Lett. 2013. PMID: 23484734
-
Zinc-mediated diastereoselective synthesis of 3-amino oxindoles by addition of methyl and terminal alkynes to N-tert-butanesulfinyl ketimines.J Org Chem. 2012 Apr 6;77(7):3311-7. doi: 10.1021/jo300110a. Epub 2012 Mar 15. J Org Chem. 2012. PMID: 22394282
-
Copper-catalyzed asymmetric alkylation of imines with dialkylzinc and related reactions.Chem Rev. 2008 Aug;108(8):2874-86. doi: 10.1021/cr078370u. Epub 2008 Jul 25. Chem Rev. 2008. PMID: 18652515 Review. No abstract available.
-
Synthesis of fluorinated chiral amines using N-tert-butylsulfinyl imines.Future Med Chem. 2009 Aug;1(5):875-88. doi: 10.4155/fmc.09.62. Future Med Chem. 2009. PMID: 21426086 Review.
Cited by
-
Enantioconvergent iso-Pictet-Spengler Reactions: Organocatalytic Synthesis of Chiral Tetrahydro-γ-carbolines.Org Lett. 2023 Jul 21;25(28):5248-5252. doi: 10.1021/acs.orglett.3c01723. Epub 2023 Jul 6. Org Lett. 2023. PMID: 37410881 Free PMC article.
-
Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction.Nat Commun. 2019 Dec 5;10(1):5553. doi: 10.1038/s41467-019-13529-z. Nat Commun. 2019. PMID: 31804483 Free PMC article.
-
A robust, efficient, and highly enantioselective method for synthesis of homopropargyl amines.Angew Chem Int Ed Engl. 2012 Jul 2;51(27):6618-21. doi: 10.1002/anie.201202694. Epub 2012 May 23. Angew Chem Int Ed Engl. 2012. PMID: 22623437 Free PMC article. No abstract available.
-
Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.Org Lett. 2015 Nov 6;17(21):5340-3. doi: 10.1021/acs.orglett.5b02692. Epub 2015 Oct 27. Org Lett. 2015. PMID: 26506430 Free PMC article.
-
Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.Molecules. 2023 Apr 11;28(8):3379. doi: 10.3390/molecules28083379. Molecules. 2023. PMID: 37110613 Free PMC article. Review.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
