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Literature DB >> 28335597

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Emma K Edelstein¹, Sheila Namirembe¹, James P Morken¹.

Abstract

Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.

Entities: Chemical Disease Gene

Year: 2017 PMID： 28335597 PMCID： PMC5620124 DOI： 10.1021/jacs.7b01774

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

21 in total

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors: Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal: Science Date: 2016-01-01 Impact factor: 47.728

2. Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

Authors: Bowman Potter; Emma K Edelstein; James P Morken
Journal: Org Lett Date: 2016-06-16 Impact factor: 6.005

3. Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

Authors: Qi Zhou; Harathi D Srinivas; Songnan Zhang; Mary P Watson
Journal: J Am Chem Soc Date: 2016-09-02 Impact factor: 15.419

4. Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors: Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal: Org Lett Date: 2010-09-03 Impact factor: 6.005

5. Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

Authors: Yang Yang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2013-07-12 Impact factor: 15.419

6. Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.

Authors: Hajime Ito; Shinichiro Ito; Yusuke Sasaki; Kou Matsuura; Masaya Sawamura
Journal: J Am Chem Soc Date: 2007-11-08 Impact factor: 15.419

7. Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters.

Authors: Jack L-Y Chen; Helen K Scott; Matthew J Hesse; Christine L Willis; Varinder K Aggarwal
Journal: J Am Chem Soc Date: 2013-03-27 Impact factor: 15.419

8. Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors: Scott N Mlynarski; Alexander S Karns; James P Morken
Journal: J Am Chem Soc Date: 2012-09-24 Impact factor: 15.419

9. Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Authors: Michael J Ardolino; James P Morken
Journal: J Am Chem Soc Date: 2014-04-29 Impact factor: 15.419

Review 10. Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

Authors: Stephen P Thomas; Rosalind M French; Vishal Jheengut; Varinder K Aggarwal
Journal: Chem Rec Date: 2009 Impact factor: 6.771

21 in total

10. Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp³) Electrophiles: Reaction Development and Application to Targets of Interest.

Authors: Seung Moh Koo; Alex J Vendola; Sarah Noemi Momm; James P Morken
Journal: Org Lett Date: 2020-01-07 Impact factor: 6.005

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

2. Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

3. Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

4. Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

5. Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

6. Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.

7. Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters.

8. Direct stereospecific amination of alkyl and aryl pinacol boronates.

9. Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Review 10. Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

1. Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

2. Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

3. Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

4. Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

5. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

6. Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

7. Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

8. Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.

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

10. Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp³) Electrophiles: Reaction Development and Application to Targets of Interest.