Literature DB >> 23321771

Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of α,α-disubstituted dihydropyrroles and studies towards an asymmetric protocol.

Adele Faulkner1, James S Scott, John F Bower.   

Abstract

We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to α,α-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.

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Year:  2013        PMID: 23321771     DOI: 10.1039/c2cc38944d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  11 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

Authors:  Feiyang Xu; Scott A Shuler; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

3.  Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors:  Feiyang Xu; Katerina M Korch; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-13       Impact factor: 15.336

4.  Heck-like Reactions Involving Heteroatomic Electrophiles.

Authors:  Bojan Vulovic; Donald A Watson
Journal:  European J Org Chem       Date:  2017-07-05

5.  Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles.

Authors:  Nicholas J Race; Ian R Hazelden; Adele Faulkner; John F Bower
Journal:  Chem Sci       Date:  2017-06-20       Impact factor: 9.825

6.  Enantioselective Narasaka-Heck cyclizations: synthesis of tetrasubstituted nitrogen-bearing stereocenters.

Authors:  Nicholas J Race; Adele Faulkner; Gabriele Fumagalli; Takayuki Yamauchi; James S Scott; Marie Rydén-Landergren; Hazel A Sparkes; John F Bower
Journal:  Chem Sci       Date:  2016-11-24       Impact factor: 9.825

7.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

8.  Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides.

Authors:  Ian R Hazelden; Xiaofeng Ma; Thomas Langer; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-27       Impact factor: 15.336

9.  Dichotomous mechanistic behavior in Narasaka-Heck cyclizations: electron rich Pd-catalysts generate iminyl radicals.

Authors:  Nicholas J Race; Adele Faulkner; Megan H Shaw; John F Bower
Journal:  Chem Sci       Date:  2015-12-01       Impact factor: 9.825

10.  Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates.

Authors:  Ian R Hazelden; Rafaela C Carmona; Thomas Langer; Paul G Pringle; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-22       Impact factor: 15.336

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