Literature DB >> 25364826

Rhodium(II)-catalyzed stereocontrolled synthesis of 2-tetrasubstituted saturated heterocycles from 1-sulfonyl-1,2,3-triazoles.

Alistair Boyer1.   

Abstract

Rhodium(II) acetate catalyzes the denitrogenative transformation of 4-substituted 1-sulfonyl-1,2,3-triazoles with pendent allyl and propargyl ethers and thioethers to onium ylides that undergo [2,3]-sigmatropic rearrangement to give 2-tetrasubstituted heterocycles with high yield and diastereoselectivity.

Entities:  

Year:  2014        PMID: 25364826     DOI: 10.1021/ol5028267

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors:  Hillary J Dequina; Jennifer M Schomaker
Journal:  Trends Chem       Date:  2020-09-02

2.  Convergent Synthesis of the C1-C29 Framework of Amphidinolide F.

Authors:  Filippo Romiti; Ludovic Decultot; J Stephen Clark
Journal:  J Org Chem       Date:  2022-06-08       Impact factor: 4.198

3.  Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.

Authors:  Steven C Schmid; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2018-07-17       Impact factor: 13.084

4.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

5.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

Authors:  Dongari Yadagiri; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825

6.  Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.

Authors:  Florian Modicom; Ellen M G Jamieson; Elise Rochette; Stephen M Goldup
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336

7.  Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D, 4-Deoxyasbestinin C, Asbestinin-10, -20, -21 and -23.

Authors:  Angus Campbell; Ian Mat Som; Claire Wilson; J Stephen Clark
Journal:  Chemistry       Date:  2020-01-16       Impact factor: 5.236

  7 in total

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