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Literature DB >> 21973180

Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Laura A Brozek¹, Michael J Ardolino, James P Morken.

Abstract

Palladium-catalyzed allyl-allyl cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl-allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).

Entities: Chemical Gene

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Year: 2011 PMID： 21973180 PMCID： PMC3219057 DOI： 10.1021/ja2075967

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

23 in total

1. Catalytic conjugate addition of allyl groups to styryl-activated enones.

Authors: Joshua D Sieber; Shubin Liu; James P Morken
Journal: J Am Chem Soc Date: 2007-02-01 Impact factor: 15.419

2. Highly regio-, diastereo-, and enantioselective Pd-catalyzed allylic alkylation of acyclic ketone enolates with monosubstituted allyl substrates.

Authors: Wen-Hua Zheng; Bao-Hui Zheng; Yan Zhang; Xue-Long Hou
Journal: J Am Chem Soc Date: 2007-06-01 Impact factor: 15.419

3. On the mechanism and selectivity of the combined C-H activation/Cope rearrangement.

Authors: Jørn H Hansen; Timothy M Gregg; Stephanie R Ovalles; Yajing Lian; Jochen Autschbach; Huw M L Davies
Journal: J Am Chem Soc Date: 2011-03-08 Impact factor: 15.419

4. A highly enantio- and diastereoselective molybdenum-catalyzed asymmetric allylic alkylation of cyanoesters.

Authors: Barry M Trost; John R Miller; Christopher M Hoffman
Journal: J Am Chem Soc Date: 2011-05-05 Impact factor: 15.419

5. On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.

Authors: Scott E Denmark; Nathan S Werner
Journal: J Am Chem Soc Date: 2010-03-17 Impact factor: 15.419

6. Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

Authors: Emmanuel Ferrer Flegeau; Uwe Schneider; Shū Kobayashi
Journal: Chemistry Date: 2009-11-16 Impact factor: 5.236

7. Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes.

Authors: Yuto Sumida; Sayuri Hayashi; Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal: Org Lett Date: 2008-03-21 Impact factor: 6.005

8. Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones.

Authors: Nathaniel H Sherden; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

9. Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.

Authors: Huw M L Davies; Qihui Jin
Journal: Proc Natl Acad Sci U S A Date: 2004-03-15 Impact factor: 11.205

10. Accurate determinations of the extent to which the SE2' reactions of allyl-, allenyl- and propargylsilanes are stereospecifically anti.

Authors: Michael J C Buckle; Ian Fleming; Salvador Gil; Kah Ling Christine Pang
Journal: Org Biomol Chem Date: 2004-02-09 Impact factor: 3.876

16 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

10. Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates.

Authors: Michael J Ardolino; Meredith S Eno; James P Morken
Journal: Adv Synth Catal Date: 2013-11-25 Impact factor: 5.837

Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

1. Catalytic conjugate addition of allyl groups to styryl-activated enones.

2. Highly regio-, diastereo-, and enantioselective Pd-catalyzed allylic alkylation of acyclic ketone enolates with monosubstituted allyl substrates.

3. On the mechanism and selectivity of the combined C-H activation/Cope rearrangement.

4. A highly enantio- and diastereoselective molybdenum-catalyzed asymmetric allylic alkylation of cyanoesters.

5. On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.

6. Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

7. Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes.

8. Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones.

9. Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.

10. Accurate determinations of the extent to which the SE2' reactions of allyl-, allenyl- and propargylsilanes are stereospecifically anti.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

2. Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: The role of ligands.

3. Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

4. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

5. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

6. Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

7. Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols.

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

9. Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

10. Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates.