Literature DB >> 26958737

Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Victoria J Garza1, Michael J Krische1.   

Abstract

Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a-1o with formaldehyde to form primary homoallylic alcohols 2a-2o with excellent control of regio- and enantioselectivity. These processes, which rely on enantiotopic π-facial discrimination of σ-allyliridium intermediates, represent the first examples of enantioselective formaldehyde C-C coupling beyond aldol addition.

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Year:  2016        PMID： 26958737      PMCID： PMC4924615          DOI： 10.1021/jacs.6b01078

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


  41 in total

1.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

2.  Hydroaminomethylation Beyond Carbonylation: Allene-Imine Reductive Coupling by Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Susumu Oda; Brannon Sam; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

3.  Paraformaldehyde and methanol as C1  feedstocks in metal-catalyzed C-C couplings of π-unsaturated reactants: beyond hydroformylation.

Authors:  Brannon Sam; Bernhard Breit; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

4.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Authors:  Pankaj Jain; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

5.  Catalytic asymmetric hydroxymethylation of silicon enolates using an aqueous solution of formaldehyde with a chiral scandium complex.

Authors:  Shunpei Ishikawa; Tomoaki Hamada; Kei Manabe; Shū Kobayashi
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

6.  Catalytic enantioselective allylboration of ketones.

Authors:  Reiko Wada; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2004-07-28       Impact factor: 15.419

7.  Organocatalytic alpha-hydroxymethylation of cyclopentanone with aqueous formaldehyde: easy access to chiral delta-lactones.

Authors:  Nobuyuki Mase; Azusa Inoue; Masaki Nishio; Kunihiko Takabe
Journal:  Bioorg Med Chem Lett       Date:  2009-03-09       Impact factor: 2.823

8.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

Authors:  Vivek Rauniyar; Huimin Zhai; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2008-06-07       Impact factor: 15.419

9.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

Authors:  Hugo Lachance; Xiaosong Lu; Michel Gravel; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2003-08-27       Impact factor: 15.419

10.  Rapid Asymmetric Transfer Hydroformylation (ATHF) of Disubstituted Alkenes Using Paraformaldehyde as a Syngas Surrogate.

Authors:  José A Fuentes; Rachael Pittaway; Matthew L Clarke
Journal:  Chemistry       Date:  2015-06-25       Impact factor: 5.236
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  11 in total

1.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

2.  Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.

Authors:  James M Cabrera; Johannes Tauber; Wandi Zhang; Ming Xiang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-18       Impact factor: 15.419

3.  Enantioselective Formation of All-Carbon Quaternary Centers via C-H Functionalization of Methanol: Iridium-Catalyzed Diene Hydrohydroxymethylation.

Authors:  Khoa D Nguyen; Daniel Herkommer; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-20       Impact factor: 15.419

4.  Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade.

Authors:  Kimberly M Hilby; Scott E Denmark
Journal:  J Org Chem       Date:  2021-10-21       Impact factor: 4.354

5.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

6.  Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl anti-(α-Aryl)allylation.

Authors:  Ming Xiang; Ankan Ghosh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

7.  Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.

Authors:  Cole C Meyer; Zachary J Dubey; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-16       Impact factor: 15.336

8.  Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer.

Authors:  Eliezer Ortiz; Jonathan Z Shezaf; Yu-Hsiang Chang; Théo P Gonçalves; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-10-04       Impact factor: 16.383

9.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

10.  Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes.

Authors:  Yangbin Liu; Daniele Fiorito; Clément Mazet
Journal:  Chem Sci       Date:  2018-05-23       Impact factor: 9.825
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