Literature DB >> 31553519

Asymmetric Alkenyl C-H Functionalization by Cpx RhIII forms 2H-Pyrrol-2-ones through [4+1]-Annulation of Acryl Amides and Allenes.

Shou-Guo Wang1, Yang Liu1,2, Nicolai Cramer1.   

Abstract

An efficient Cpx RhIII -catalyzed enantioselective alkenyl C-H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β-unsaturated-γ-lactams bearing a quaternary stereocenter. The reaction operates under mild conditions, displays a broad functional-group tolerance, and provides 2H-pyrrol-2-ones with excellent selectivity of up to 97:3 er. Such scaffolds are frequently found in natural products and synthetic bioactive compounds and are of significant synthetic value. It is noteworthy that the allene serves as a one-carbon unit in the [4+1]-annulation.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; [4+1]-annulation; asymmetric catalysis; chiral Cp ligands; rhodium

Year:  2019        PMID: 31553519     DOI: 10.1002/anie.201909971

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

2.  Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors:  Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal:  Organic Synth       Date:  2021

3.  Rh(iii)-Catalyzed [5 + 1] annulation of 2-alkenylanilides and 2-alkenylphenols with allenyl acetates.

Authors:  Anurag Singh; Rahul K Shukla; Chandra M R Volla
Journal:  Chem Sci       Date:  2022-01-19       Impact factor: 9.825

  3 in total

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