Literature DB >> 25642639

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

Gia L Hoang1, Zhao-Di Yang, Sean M Smith, Rhitankar Pal, Judy L Miska, Damaris E Pérez, Libbie S W Pelter, Xiao Cheng Zeng, James M Takacs.   

Abstract

The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

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Year:  2015        PMID： 25642639      PMCID： PMC4385711          DOI： 10.1021/ol503764d

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


  50 in total

1.  Catalytic enantioselective reductive desymmetrisation of achiral and meso compounds.

Authors:  Héctor Fernández-Pérez; Pablo Etayo; Joan R Lao; José L Núñez-Rico; Anton Vidal-Ferran
Journal:  Chem Commun (Camb)       Date:  2013-11-25       Impact factor: 6.222

2.  Catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides: striking influence of the borane.

Authors:  Sean M Smith; Maulen Uteuliyev; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2011-06-03       Impact factor: 6.222

3.  Stereospecific couplings of secondary and tertiary boronic esters.

Authors:  Daniele Leonori; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-20       Impact factor: 15.336

4.  γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2012-12-28       Impact factor: 6.222

5.  Remarkable levels of enantioswitching in catalytic asymmetric hydroboration.

Authors:  Sean M Smith; James M Takacs
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

6.  Catalytic enantioselective hydroboration of cyclopropenes.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419

7.  Rh-catalyzed addition of β-carbonyl pinacol alkylboronates to aldehydes: asymmetric synthesis of γ-butyrolactones.

Authors:  Changwan Zhang; Jaesook Yun
Journal:  Org Lett       Date:  2013-06-17       Impact factor: 6.005

8.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

9.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

10.  Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors:  Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
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  12 in total

1.  Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran E and Other Targets of Interest.

Authors:  Thomas P Blaisdell; James P Morken
Journal:  J Am Chem Soc       Date:  2015-07-02       Impact factor: 15.419

2.  Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors:  Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal:  Nat Rev Chem       Date:  2020-09-24       Impact factor: 34.035

3.  Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.

Authors:  G L Hoang; S Zhang; J M Takacs
Journal:  Chem Commun (Camb)       Date:  2018-05-08       Impact factor: 6.222

4.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

5.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

6.  Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; James M Takacs
Journal:  Chem Sci       Date:  2017-05-03       Impact factor: 9.825

7.  Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes.

Authors:  Suman Chakrabarty; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-20       Impact factor: 15.419

8.  Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.

Authors:  Veronika M Shoba; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-17       Impact factor: 15.419

9.  Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with aryl boronic acids.

Authors:  Honggui Lv; Li-Jun Xiao; Dongbing Zhao; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2018-07-18       Impact factor: 9.825

10.  Chiral Aniline Synthesis via Stereospecific C(sp3)-C(sp2) Coupling of Boronic Esters with Aryl Hydrazines.

Authors:  Venkataraman Ganesh; Adam Noble; Varinder K Aggarwal
Journal:  Org Lett       Date:  2018-09-17       Impact factor: 6.005
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