Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines
- PMID: 17949100
- DOI: 10.1021/ol7022104
Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines
Abstract
The reaction of the dienolate of ethyl acetoacetate (and related dienolates) with a range of 1,2- and 1,3-cyclic sulfamidates provides an entry to substituted and enantiopure alkylidenated pyrrolidines and piperidines. These heterocycles function as convenient precursors to heterocyclic beta-amino acid derivatives.
Similar articles
-
Tantalum catalyzed hydroaminoalkylation for the synthesis of α- and β-substituted N-heterocycles.Org Lett. 2013 May 3;15(9):2182-5. doi: 10.1021/ol400729v. Epub 2013 Apr 19. Org Lett. 2013. PMID: 23600625
-
Determining the scope of the organolanthanide-catalyzed, sequential intramolecular amination/cyclization reaction: formation of substituted quinolizidines, indolizidines, and pyrrolizidines.J Org Chem. 2003 Nov 28;68(24):9214-20. doi: 10.1021/jo035205f. J Org Chem. 2003. PMID: 14629138
-
Stereospecific rearrangements during the synthesis of pyrrolidines and related heterocycles from cyclizations of amino alcohols with vinyl Sulfones.J Org Chem. 2003 Nov 28;68(24):9389-93. doi: 10.1021/jo0350864. J Org Chem. 2003. PMID: 14629162
-
[Asymmetric intramolecular conjugate addition of chiral enolates via non-equilibrium].Yakugaku Zasshi. 2006 Aug;126(8):617-27. doi: 10.1248/yakushi.126.617. Yakugaku Zasshi. 2006. PMID: 16880720 Review. Japanese.
-
Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives.Molecules. 2017 Mar 19;22(3):483. doi: 10.3390/molecules22030483. Molecules. 2017. PMID: 28335499 Free PMC article. Review.
Cited by
-
A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.Angew Chem Int Ed Engl. 2009;48(21):3802-5. doi: 10.1002/anie.200806292. Angew Chem Int Ed Engl. 2009. PMID: 19378315 Free PMC article.
-
Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Sulfamidate Imines: Efficient Synthesis of Chiral Cyclic Sulfamidates.iScience. 2019 Sep 27;19:63-73. doi: 10.1016/j.isci.2019.07.004. Epub 2019 Jul 4. iScience. 2019. PMID: 31352194 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources