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Literature DB >> 24839434

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

Michael J Ardolino¹, Meredith S Eno¹, James P Morken¹.

Abstract

Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral Palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple readily available starting materials.

Entities: Chemical Disease Gene

Keywords: Allylation; Asymmetric Catalysis; Asymmetric Synthesis; Boron; Palladium

Year: 2013 PMID： 24839434 PMCID： PMC4019443 DOI： 10.1002/adsc.201300720

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

31 in total

1. Dynamic Kinetic Resolution of Acyclic Allylic Acetates Using Lipase and Palladium.

Authors: Yoon Kyung Choi; Jong Hwa Suh; Donghyun Lee; In Taek Lim; Jae Yoon Jung; Mahn-Joo Kim
Journal: J Org Chem Date: 1999-10-29 Impact factor: 4.354

2. On the interpretation of deuterium kinetic isotope effects in C-H bond functionalizations by transition-metal complexes.

Authors: Eric M Simmons; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2012-03-05 Impact factor: 15.336

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

Authors: Michael J Ardolino; James P Morken
Journal: J Am Chem Soc Date: 2012-05-17 Impact factor: 15.419

4. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors:
Journal: Phys Rev B Condens Matter Date: 1988-01-15

5. Palladium-catalyzed cyanation of propargylic carbonates with trimethylsilyl cyanide

Authors:
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

6. Cationic rhodium(I)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to alpha,beta-enones.

Authors: Ken Tanaka; Takeaki Shoji
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

7. Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole.

Authors: Vladimir B Birman; Lei Guo
Journal: Org Lett Date: 2006-10-12 Impact factor: 6.005

8. Nickel-catalyzed enantioselective cross-couplings of racemic secondary electrophiles that bear an oxygen leaving group.

Authors: Alexander J Oelke; Jianwei Sun; Gregory C Fu
Journal: J Am Chem Soc Date: 2012-02-01 Impact factor: 15.419

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

Authors: Laura A Brozek; Michael J Ardolino; James P Morken
Journal: J Am Chem Soc Date: 2011-10-05 Impact factor: 15.419

10. Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors: Gary A Molander; Erin M Sommers; Sharon R Baker
Journal: J Org Chem Date: 2006-02-17 Impact factor: 4.354

5 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