Literature DB >> 17340001

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

Olivier Riant1, Jérôme Hannedouche.   

Abstract

There is a growing need in organic synthesis for efficient methodologies for the asymmetric synthesis of quaternary carbon centres. One of the most attractive and straightforward methods focuses on the use of asymmetric catalysis for the addition of various types of nucleophiles on prochiral ketones and ketimines. A view of the literature from this growing area of research will be presented in this review, with an emphasis on the pioneer works and milestones brought by the main players in this field.

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Year:  2007        PMID: 17340001     DOI: 10.1039/b617746h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  38 in total

1.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

Review 2.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

3.  Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

Authors:  Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

4.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

5.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

6.  Screening and Identification of Metacaspase Inhibitors: Evaluation of Inhibition Mechanism and Trypanocidal Activity.

Authors:  Brian Pérez; León A Bouvier; Juan José Cazzulo; Fernán Agüero; Emir Salas-Sarduy; Vanina E Alvarez
Journal:  Antimicrob Agents Chemother       Date:  2021-02-17       Impact factor: 5.191

7.  Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: iridium-catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Junji Itoh; Soo Bong Han; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

9.  Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines.

Authors:  Hwanjong Jang; Filippo Romiti; Sebastian Torker; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-07-17       Impact factor: 24.427

10.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

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