Literature DB >> 22350584

Iridium-Catalyzed Allylic Amination Route to α-Aminoboronates: Illustration of the Decisive Role of Boron Substituents.

Sabrina Touchet1, François Carreaux, Gary A Molander, Bertrand Carboni, Alexandre Bouillon.   

Abstract

The development of a new route to α-aminoboronates using an iridium-catalyzed allylic amination on boronated substrates is described. Unlike the boronate group, the trifluoroborato substituent was found to govern the regioselectivity exclusively in favor of branched products. The transformation of an allylic substitution product into an α-aminoboronic ester in an efficient way validated the implementation of this approach.

Entities:  

Year:  2011        PMID： 22350584      PMCID： PMC3281748          DOI： 10.1002/adsc.201100407

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  26 in total

1.  Ir-catalysed asymmetric allylic substitutions with cyclometalated (phosphoramidite)Ir complexes--resting states, catalytically active (pi-allyl)Ir complexes and computational exploration.

Authors:  Jevgenij A Raskatov; Stephanie Spiess; Christian Gnamm; Kerstin Brödner; Frank Rominger; Günter Helmchen
Journal:  Chemistry       Date:  2010-06-11       Impact factor: 5.236

2.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

3.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

Review 4.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

5.  Allylic substitution versus Suzuki cross-coupling: capitalizing on chemoselectivity with bifunctional substrates.

Authors:  Mahmud M Hussain; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-01       Impact factor: 15.336

6.  Synthesis and evaluation of new omega-borono-alpha-amino acids as rat liver arginase inhibitors.

Authors:  Olivier Busnel; François Carreaux; Bertrand Carboni; Stephanie Pethe; Sandrine Vadon-Le Goff; Daniel Mansuy; Jean-Luc Boucher
Journal:  Bioorg Med Chem       Date:  2005-04-01       Impact factor: 3.641

7.  Phase II trial of single agent Val-boroPro (Talabostat) inhibiting Fibroblast Activation Protein in patients with metastatic colorectal cancer.

Authors:  Kalyani Narra; Stefanie R Mullins; Hyung-Ok Lee; Brenda Strzemkowski-Brun; Kimberly Magalong; Victoria J Christiansen; Patrick A McKee; Brian Egleston; Steven J Cohen; Louis M Weiner; Neal J Meropol; Jonathan D Cheng
Journal:  Cancer Biol Ther       Date:  2007-08-14       Impact factor: 4.742

8.  Diastereo- and enantiomerically pure allylboronates: their synthesis and scope.

Authors:  Jörg Pietruszka; Niklas Schöne; Wolfgang Frey; Li Grundl
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  Asymmetric copper-catalyzed synthesis of alpha-amino boronate esters from N-tert-butanesulfinyl aldimines.

Authors:  Melissa A Beenen; Chihui An; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

Review 10.  alpha-Amido boronic acids: a synthetic challenge and their properties as serine protease inhibitors.

Authors:  Donald S Matteson
Journal:  Med Res Rev       Date:  2008-03       Impact factor: 12.944
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  4 in total

1.  Breaking Conjugation: Unusual Regioselectivity with 2-Substituted Allylic Substrates in the Tsuji-Trost Reaction.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Per-Ola Norrby; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-03       Impact factor: 9.825

2.  Palladium-catalyzed chemoselective allylic substitution, Suzuki-Miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Nusrah Hussain; Patrick J Walsh
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

3.  Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Authors:  Yazhou Lou; Jun Wang; Gelin Gong; Fanfu Guan; Jiaxiang Lu; Jialin Wen; Xumu Zhang
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

Review 4.  Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.

Authors:  Ugo Azzena; Massimo Carraro; Luisa Pisano; Serena Monticelli; Roberta Bartolotta; Vittorio Pace
Journal:  ChemSusChem       Date:  2018-11-20       Impact factor: 8.928
  4 in total

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