Literature DB >> 20407730

Synthetic applications of rhodium catalysed conjugate addition.

Hannah J Edwards1, Jonathan D Hargrave, Stephen D Penrose, Christopher G Frost.   

Abstract

The rhodium catalysed conjugate addition of organometallics to activated alkenes is a powerful synthetic tool for establishing new carbon-carbon bonds often with high stereoselectivity. The introduction of a practical, efficient method for introducing functionalised aryl and alkenyl fragments with predictable stereocontrol has caught the attention of synthetic chemists and emerging examples are growing in number and complexity. In this tutorial review, we document notable advances in the application of rhodium catalysed conjugate addition processes within the context of synthesis of complex molecules and intermediates in drug discovery. The chosen examples illustrate important issues regarding scope, selectivity and reactivity that will help guide the selection of appropriate donor and acceptor to achieve the desired carbon-carbon bond construction when planning new synthetic routes.

Entities:  

Year:  2010        PMID: 20407730     DOI: 10.1039/b919762c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  21 in total

1.  Rhodium-Catalyzed Asymmetric 1,4-Additions, in Water at Room Temperature, with In-Flask Catalyst Recycling.

Authors:  Bruce H Lipshutz; Nicholas A Isley; Ralph Moser; Subir Ghorai; Helena Leuser; Benjamin R Taft
Journal:  Adv Synth Catal       Date:  2012-11-26       Impact factor: 5.837

2.  Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors:  Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

3.  Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones.

Authors:  Antoinette E Nibbs; Karl A Scheidt
Journal:  European J Org Chem       Date:  2011-12-09

4.  Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Authors:  Christian A Malapit; Irungu K Luvaga; Donald R Caldwell; Nicholas K Schipper; Amy R Howell
Journal:  Org Lett       Date:  2017-08-15       Impact factor: 6.005

Review 5.  Dehydroamino acids: chemical multi-tools for late-stage diversification.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

Review 6.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

7.  Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition.

Authors:  Michael L Conner; M Kevin Brown
Journal:  J Org Chem       Date:  2016-08-25       Impact factor: 4.354

Review 8.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

9.  Enthalpy vs Entropy Driven Complexation of Homoallylic Alcohols by Rh(I) Complexes.

Authors:  Sung Ok Kang; Vincent M Lynch; Victor W Day; Eric V Anslyn
Journal:  Organometallics       Date:  2011-10-25       Impact factor: 3.876

10.  Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids.

Authors:  Hanna M Key; Scott J Miller
Journal:  J Am Chem Soc       Date:  2017-10-20       Impact factor: 15.419

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