Literature DB >> 26511715

Synthesis of Chiral Tertiary Alcohols by Cu(I) -Catalyzed Enantioselective Addition of Organomagnesium Reagents to Ketones.

Jiawei Rong1, Tilde Pellegrini1, Syuzanna R Harutyunyan2.   

Abstract

Catalytic enantioselective addition of organometallic nucleophiles to ketones is among the most straightforward approaches to the synthesis of chiral tertiary alcohols. The first such catalytic methodologies using the highly reactive organomagnesium reagents, which are the preferred organometallic reagents in terms of cost, availability, atom efficiency, and structural diversity, were developed only during the last five years. This Concept article highlights the fundamental breakthrough that made the development of methodologies for highly enantioselective Cu(I) -catalyzed alkylation of ketones using organomagnesium reagents possible.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Grignard reagents; alcohols; asymmetric amplification; copper; homogeneous catalysis

Year:  2015        PMID: 26511715     DOI: 10.1002/chem.201503412

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  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

2.  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

3.  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

4.  Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones.

Authors:  Harley Green; Stephen P Argent; Hon Wai Lam
Journal:  Chemistry       Date:  2021-03-05       Impact factor: 5.236

5.  Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides.

Authors:  Mercedes Zurro; Luo Ge; Syuzanna R Harutyunyan
Journal:  Org Lett       Date:  2022-09-02       Impact factor: 6.072

  5 in total

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