Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Literature DB >> 32212403

Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Chunyin Law¹, Elton Kativhu¹, Johnny Wang¹, James P Morken¹.

Abstract

Enantioselective conjunctive cross-coupling of enyne-derived boronate complexes occurs with 1,4 addition of the electrophile and migrating group across the π system. This reaction pathway furnishes α-boryl allenes as the reaction product. In the presence of a chiral catalyst, both the central and axial chirality of the product can be controlled during product formation.

Entities: Chemical

Keywords: boronates; chirality; cross-coupling; homogeneous catalysis; palladium

Mesh：

Substances：

Year: 2020 PMID： 32212403 PMCID： PMC7473481 DOI： 10.1002/anie.202001580

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

46 in total

1. Enantioselective synthesis of and with allenes.

Authors: Anja Hoffmann-Röder; Norbert Krause
Journal: Angew Chem Int Ed Engl Date: 2002-08-16 Impact factor: 15.336

2. Some typical advances in the synthetic applications of allenes.

Authors: Shengming Ma
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

3. Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction.

Authors: Aurélien Tap; Aurélie Blond; Vijay N Wakchaure; Benjamin List
Journal: Angew Chem Int Ed Engl Date: 2016-06-08 Impact factor: 15.336

4. Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans.

Authors: A Hoffmann-Röder; N Krause
Journal: Org Lett Date: 2001-08-09 Impact factor: 6.005

5. Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives.

Authors: Pernille H Poulsen; Yang Li; Vibeke H Lauridsen; Danny K B Jørgensen; Teresa A Palazzo; Marta Meazza; Karl Anker Jørgensen
Journal: Angew Chem Int Ed Engl Date: 2018-07-13 Impact factor: 15.336

6. Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors: Matteo Chierchia; Chunyin Law; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2017-08-17 Impact factor: 15.336

7. Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the alpha-carbon atom.

Authors: Shengming Ma
Journal: Acc Chem Res Date: 2003-09 Impact factor: 22.384

8. Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

Authors: Takuya Hashimoto; Kazuki Sakata; Fumiko Tamakuni; Mark J Dutton; Keiji Maruoka
Journal: Nat Chem Date: 2013-02-10 Impact factor: 24.427

9. Nucleophilic transition metal based cyclization of allenes.

Authors: Roderick W Bates; Vachiraporn Satcharoen
Journal: Chem Soc Rev Date: 2002-01 Impact factor: 54.564

10. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors: Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2018-02-08 Impact factor: 15.419

6 in total

Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

1. Enantioselective synthesis of and with allenes.

2. Some typical advances in the synthetic applications of allenes.

3. Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction.

4. Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans.

5. Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives.

6. Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

7. Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the alpha-carbon atom.

8. Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

9. Nucleophilic transition metal based cyclization of allenes.

10. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

1. Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

2. Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.

3. Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration.

4. Parahydrogen-Induced Polarization in Hydrogenation Reactions Mediated by a Metal-Free Catalyst.

5. Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis.

6. Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement.