Literature DB >> 23363050

Regio- and enantioselective synthesis of pyrrolidines bearing a quaternary center by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethanes.

Barry M Trost1, Tom M Lam, Melissa A Herbage.   

Abstract

Herein we describe the first use of disubstituted donors in the palladium-catalyzed trimethylenemethane (TMM) cycloaddition resulting in an enantioselective synthesis of highly substituted pyrrolidines. These cyanoalkyl donors 1 form all-carbon quaternary centers in a catalytic, asymmetric, and intermolecular manner uniquely using diamidophosphite ligands L2 and L3, generating synthetically important chiral building blocks in good yields and selectivities.

Entities:  

Year:  2013        PMID: 23363050     DOI: 10.1021/ja312351s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl-Alkyl Cross-Coupling.

Authors:  Xin Mu; Yu Shibata; Yusuke Makida; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-19       Impact factor: 15.336

2.  Successive Nucleophilic and Electrophilic Allylation for the Catalytic Enantioselective Synthesis of 2,4-Disubstituted Pyrrolidines.

Authors:  Guoshun Luo; Ming Xiang; Michael J Krische
Journal:  Org Lett       Date:  2019-02-28       Impact factor: 6.005

3.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

4.  Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: catalytic asymmetric Negishi α-alkylations of N-Boc-pyrrolidine.

Authors:  Christopher J Cordier; Rylan J Lundgren; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2013-07-19       Impact factor: 15.419

5.  Ligand-enabled multiple absolute stereocontrol in metal-catalysed cycloaddition for construction of contiguous all-carbon quaternary stereocentres.

Authors:  Kohsuke Ohmatsu; Naomichi Imagawa; Takashi Ooi
Journal:  Nat Chem       Date:  2013-11-24       Impact factor: 24.427

Review 6.  Strategies for the Syntheses of Pactamycin and Jogyamycin.

Authors:  Nels C Gerstner; Kate A Nicastri; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-18       Impact factor: 15.336

7.  Highly substituted enantioenriched cyclopentane derivatives by palladium-catalyzed [3 + 2] trimethylenemethane cycloadditions with disubstituted nitroalkenes.

Authors:  Barry M Trost; Dustin A Bringley; B Michael O'Keefe
Journal:  Org Lett       Date:  2013-10-25       Impact factor: 6.005

8.  Rapid access to spirocyclic oxindole alkaloids: application of the asymmetric palladium-catalyzed [3 + 2] trimethylenemethane cycloaddition.

Authors:  Barry M Trost; Dustin A Bringley; Ting Zhang; Nicolai Cramer
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

9.  One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.

Authors:  David M Barber; Andrej Duriš; Amber L Thompson; Hitesh J Sanganee; Darren J Dixon
Journal:  ACS Catal       Date:  2014-01-06       Impact factor: 13.084

10.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

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