Literature DB >> 23763463

Catalytic enantioselective one-pot aminoborylation of aldehydes: a strategy for construction of nonracemic α-amino boronates.

Kai Hong1, James P Morken.   

Abstract

We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)2 across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl α-amino boronic ester derivatives.

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Year:  2013        PMID: 23763463      PMCID: PMC3752158          DOI: 10.1021/ja402569j

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


  26 in total

Review 1.  Building on bortezomib: second-generation proteasome inhibitors as anti-cancer therapy.

Authors:  Lawrence R Dick; Paul E Fleming
Journal:  Drug Discov Today       Date:  2010-01-29       Impact factor: 7.851

2.  Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes.

Authors:  Irina Beletskaya; Christina Moberg
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

3.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Authors:  Laura T Kliman; Scott N Mlynarski; Grace E Ferris; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-01       Impact factor: 15.336

5.  Platinum-catalyzed diboration using a commercially available catalyst: diboration of aldimines to alpha-aminoboronate esters

Authors: 
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

Review 6.  Development of the proteasome inhibitor Velcade (Bortezomib).

Authors:  Julian Adams; Michael Kauffman
Journal:  Cancer Invest       Date:  2004       Impact factor: 2.176

7.  Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors:  Laura T Kliman; Scott N Mlynarski; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

Review 8.  Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors:  Heather E Burks; James P Morken
Journal:  Chem Commun (Camb)       Date:  2007-08-22       Impact factor: 6.222

9.  Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

Authors:  Tatsuo Ishiyama; Norio Miyaura
Journal:  Chem Rec       Date:  2004       Impact factor: 6.771

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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  17 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Org Lett       Date:  2015-02-02       Impact factor: 6.005

3.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

4.  Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors:  Suttipol Radomkit; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

5.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

6.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

7.  Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.

Authors:  Corey H Basch; Kelsey M Cobb; Mary P Watson
Journal:  Org Lett       Date:  2015-12-17       Impact factor: 6.005

8.  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

9.  Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines.

Authors:  Jian-Bo Xie; Jian Luo; Timothy R Winn; David B Cordes; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-31       Impact factor: 2.883

10.  Silyl imine electrophiles in enantioselective catalysis: a Rosetta Stone for peptide homologation, enabling diverse N-protected aryl glycines from aldehydes in three steps.

Authors:  Dawn M Makley; Jeffrey N Johnston
Journal:  Org Lett       Date:  2014-05-14       Impact factor: 6.005

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