Literature DB >> 25403641

Catalytic asymmetric alkylation of acylsilanes.

Jiawei Rong1, Rik Oost, Alaric Desmarchelier, Adriaan J Minnaard, Syuzanna R Harutyunyan.   

Abstract

The highly enantioselective addition of Grignard reagents to acylsilanes is catalyzed by copper diphosphine complexes. This transformation affords α-silylated tertiary alcohols in up to 97% yield and 98:2 enantiomeric ratio. The competing Meerwein-Ponndorf-Verley reduction is suppressed by the use of a mixture of Lewis acid additives. The chiral catalyst can be recovered as a copper complex and used repeatedly without any loss of catalytic activity.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Grignard reactions; acylsilanes; alkylation; asymmetric synthesis; copper catalysis

Year:  2014        PMID: 25403641     DOI: 10.1002/anie.201409815

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  7 in total

1.  Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines.

Authors:  Jiawei Rong; Juan F Collados; Pablo Ortiz; Ravindra P Jumde; Edwin Otten; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2016-12-23       Impact factor: 14.919

2.  Catalytic enantioselective addition of organometallics to unprotected carboxylic acids.

Authors:  Xingchen Yan; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2019-07-30       Impact factor: 14.919

3.  Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors.

Authors:  Yafei Guo; Syuzanna R Harutyunyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

4.  Direct synthesis and applications of solid silylzinc reagents.

Authors:  Revathi Chandrasekaran; Feba Thomas Pulikkottil; Krishna Suresh Elama; Ramesh Rasappan
Journal:  Chem Sci       Date:  2021-11-30       Impact factor: 9.825

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

6.  π-Extended Polyaromatic Hydrocarbons by Sustainable Alkyne Annulations through Double C-H/N-H Activation.

Authors:  Elżbieta Gońka; Long Yang; Ralf Steinbock; Fabio Pesciaioli; Rositha Kuniyil; Lutz Ackermann
Journal:  Chemistry       Date:  2019-12-09       Impact factor: 5.236

7.  Nucleophilic Dearomatization of N-Heteroaromatics Enabled by Lewis Acids and Copper Catalysis.

Authors:  Xingchen Yan; Luo Ge; Marta Castiñeira Reis; Syuzanna R Harutyunyan
Journal:  J Am Chem Soc       Date:  2020-11-10       Impact factor: 15.419

  7 in total

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