Literature DB >> 16986952

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.

Frederic Menard1, Timothy M Chapman, Chris Dockendorff, Mark Lautens.   

Abstract

An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH]2 and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to >20:1.

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Year:  2006        PMID: 16986952     DOI: 10.1021/ol061777l

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


  6 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Rhodium-catalysed asymmetric allylic arylation of racemic halides with arylboronic acids.

Authors:  Mireia Sidera; Stephen P Fletcher
Journal:  Nat Chem       Date:  2015-10-12       Impact factor: 24.427

3.  Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Authors:  Harathi D Srinivas; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005

4.  Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents.

Authors:  Shermin S Goh; Sureshbabu Guduguntla; Takashi Kikuchi; Martin Lutz; Edwin Otten; Makoto Fujita; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2018-05-31       Impact factor: 15.419

5.  Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes.

Authors:  Yi-Ming Wang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-04-07       Impact factor: 15.419

6.  Desymmetrization of meso-bisphosphates using copper catalysis and alkylzirconocene nucleophiles.

Authors:  Reece Jacques; Robert D C Pullin; Stephen P Fletcher
Journal:  Nat Commun       Date:  2019-01-03       Impact factor: 14.919

  6 in total

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