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Literature DB >> 31490591

Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

Gilmar A Brito¹, Woo-Ok Jung¹, Minjin Yoo¹, Michael J Krische¹.

Abstract

Highly enantioselective catalytic reductive coupling of allyl acetate with acetylenic ketones occurs in a chemoselective manner in the presence of aliphatic or aromatic ketones. This method was used to construct C14-C23 of pladienolide D in half the steps previously required.

Entities: Chemical Disease Gene Species

Keywords: enantioselectivity; iridium; ketone allylation; transfer hydrogenation; π-allyl

Mesh：

Substances：

Year: 2019 PMID： 31490591 PMCID： PMC6917958 DOI： 10.1002/anie.201908939

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

41 in total

1. Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level.

Authors: John F Bower; Eduardas Skucas; Ryan L Patman; Michael J Krische
Journal: J Am Chem Soc Date: 2007-11-17 Impact factor: 15.419

Review 2. Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines.

Authors: Olivier Riant; Jérôme Hannedouche
Journal: Org Biomol Chem Date: 2007-02-05 Impact factor: 3.876

3. Synthesis of Chiral Tertiary Alcohols by Cu(I) -Catalyzed Enantioselective Addition of Organomagnesium Reagents to Ketones.

Authors: Jiawei Rong; Tilde Pellegrini; Syuzanna R Harutyunyan
Journal: Chemistry Date: 2015-10-29 Impact factor: 5.236

4. Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Authors: Abbas Hassan; Ian A Townsend; Michael J Krische
Journal: Chem Commun (Camb) Date: 2011-08-10 Impact factor: 6.222

5. Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic enones.

Authors: Jeung Gon Kim; Karen M Waltz; Iliana F Garcia; David Kwiatkowski; Patrick J Walsh
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

6. Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities.

Authors: Yoshiharu Mizui; Takashi Sakai; Masao Iwata; Toshimitsu Uenaka; Kiyoshi Okamoto; Hajime Shimizu; Takao Yamori; Kentaro Yoshimatsu; Makoto Asada
Journal: J Antibiot (Tokyo) Date: 2004-03 Impact factor: 2.649

Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

1. Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level.

Review 2. Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines.

3. Synthesis of Chiral Tertiary Alcohols by Cu(I) -Catalyzed Enantioselective Addition of Organomagnesium Reagents to Ketones.

4. Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

5. Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic enones.

6. Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities.

7. Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.

8. Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling.

9. Platinum(II) Enyne Cycloisomerization Catalysis: Intermediates and Resting States.

10. Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates.

1. Electroreductive Olefin-Ketone Coupling.

Review 2. Total Syntheses of Pladienolide-Derived Spliceosome Modulators.