Literature DB >> 16220945

Catalytic enantioselective conjugate reduction of lactones and lactams.

Gregory Hughes1, Masanari Kimura, Stephen L Buchwald.   

Abstract

A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl(2).H(2)O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.

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Year:  2003        PMID: 16220945     DOI: 10.1021/ja0351692

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


  29 in total

1.  Dimerization of (+)-Myrmicarin 215B. A Potential Biomimetic Approach to Complex Myrmicarin Alkaloids.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Tetrahedron       Date:  2006-05-29       Impact factor: 2.457

2.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

3.  CuH-catalyzed enantioselective 1,2-reductions of alpha,beta-unsaturated ketones.

Authors:  Ralph Moser; Zarko V Bosković; Christopher S Crowe; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

4.  Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

5.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

6.  CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.

Authors:  Yujing Zhou; Jeffrey S Bandar; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

7.  CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

Authors:  Achim Link; Yujing Zhou; Stephen L Buchwald
Journal:  Org Lett       Date:  2020-07-06       Impact factor: 6.005

8.  Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration.

Authors:  Andrew DeAngelis; Robert Panish; Joseph M Fox
Journal:  Acc Chem Res       Date:  2015-12-21       Impact factor: 22.384

9.  Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

Authors:  Nicholas A White; Kerem E Ozboya; Darrin M Flanigan; Tomislav Rovis
Journal:  Asian J Org Chem       Date:  2014-04       Impact factor: 3.319

10.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

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