Literature DB >> 22473044

Consecutive iridium catalyzed C-C and C-H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C-H (2-fluoro)allylation of primary alcohols.

Abbas Hassan1, T Patrick Montgomery, Michael J Krische.   

Abstract

Commercially available (2-fluoro)allyl chloride serves as an efficient allyl donor in highly enantioselective iridium catalyzed carbonyl (2-fluoro)allylations from the alcohol or aldehyde oxidation level via transfer hydrogenation. Diastereoselective Crabtree hydrogenation of the resulting homoallylic alcohols provides syn-3-fluoro-1-alcohols. This journal is © The Royal Society of Chemistry 2012

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Year:  2012        PMID： 22473044      PMCID： PMC3448947          DOI： 10.1039/c2cc31743e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  29 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

Review 2.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

Review 3.  Asymmetric synthesis of active pharmaceutical ingredients.

Authors:  Vittorio Farina; Jonathan T Reeves; Chris H Senanayake; Jinhua J Song
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

4.  Creation of quaternary stereocenters in carbonyl allylation reactions.

Authors:  Ilan Marek; Genia Sklute
Journal:  Chem Commun (Camb)       Date:  2006-12-06       Impact factor: 6.222

5.  Catalytic asymmetric fluorination comes of age.

Authors:  Vincent A Brunet; David O'Hagan
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  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

7.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

8.  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

9.  Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst.

Authors:  Xin Gao; Ian A Townsend; Michael J Krische
Journal:  J Org Chem       Date:  2011-03-04       Impact factor: 4.354

10.  1,n-glycols as dialdehyde equivalents in iridium-catalyzed enantioselective carbonyl allylation and iterative two-directional assembly of 1,3-polyols.

Authors:  Yu Lu; In Su Kim; Abbas Hassan; David J Del Valle; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  5 in total

1.  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

2.  Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive.

Authors:  Yuxuan Ye; Takashi Takada; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-15       Impact factor: 15.336

3.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

4.  Ruthenium catalyzed reductive coupling of paraformaldehyde to trifluoromethyl allenes: CF3-bearing all-carbon quaternary centers.

Authors:  Brannon Sam; T Patrick Montgomery; Michael J Krische
Journal:  Org Lett       Date:  2013-07-10       Impact factor: 6.005

5.  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
  5 in total

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