Literature DB >> 29938513

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

Gilmar A Brito1,2, Franco Della-Felice1,2, Guoshun Luo1, Alexander S Burns3, Ronaldo A Pilli2, Scott D Rychnovsky3, Michael J Krische1.   

Abstract

Cyclometalated π-allyliridium C,O-benzoates modified by ( S)-SEGPHOS or ( S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSC≡CCHO. Absolute stereochemistries of the resulting secondary homoallylic-propargylic alcohols were assigned using Rychnovsky's competing enantioselective conversion method.

Entities:  

Year:  2018        PMID： 29938513      PMCID： PMC6205292          DOI： 10.1021/acs.orglett.8b01776

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  30 in total

1.  Modular synthesis of the C9-C27 degradation product of aflastatin A via alkyne-epoxide cross-couplings.

Authors:  Omar Robles; Frank E McDonald
Journal:  Org Lett       Date:  2008-04-10       Impact factor: 6.005

2.  Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors:  Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal:  Chem Rev       Date:  2011-09-16       Impact factor: 60.622

3.  Enantioselective Total Synthesis of Mandelalide A and Isomandelalide A: Discovery of a Cytotoxic Ring-Expanded Isomer.

Authors:  Nagarathanam Veerasamy; Ankan Ghosh; Jinming Li; Kazuhiro Watanabe; Jeffrey D Serrill; Jane E Ishmael; Kerry L McPhail; Rich G Carter
Journal:  J Am Chem Soc       Date:  2016-01-13       Impact factor: 15.419

4.  Nanomole-Scale Assignment and One-Use Kits for Determining the Absolute Configuration of Secondary Alcohols.

Authors:  Alexander J Wagner; Shawn M Miller; Ryan P King; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2016-07-14       Impact factor: 4.354

5.  Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.

Authors:  Daniel C Schmitt; Anne-Marie R Dechert-Schmitt; Michael J Krische
Journal:  Org Lett       Date:  2012-12-11       Impact factor: 6.005

6.  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

7.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

8.  Determination of absolute configuration using kinetic resolution catalysts.

Authors:  Alexander J Wagner; Jonathan G David; Scott D Rychnovsky
Journal:  Org Lett       Date:  2011-07-21       Impact factor: 6.005

9.  Homobenzotetramisole: an effective catalyst for kinetic resolution of aryl-cycloalkanols.

Authors:  Vladimir B Birman; Ximin Li
Journal:  Org Lett       Date:  2008-02-16       Impact factor: 6.005

10.  Elongation of 1,3-polyols via iterative catalyst-directed carbonyl allylation from the alcohol oxidation level.

Authors:  Abbas Hassan; Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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  5 in total

1.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

2.  Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling.

Authors:  Franco Della-Felice; Ariel M Sarotti; Michael J Krische; Ronaldo A Pilli
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

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

Authors:  Gilmar A Brito; Woo-Ok Jung; Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

4.  Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation.

Authors:  Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-11       Impact factor: 16.823

5.  Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.

Authors:  Yuk-Ming Siu; James Roane; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-07-08       Impact factor: 16.383
  5 in total

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