Literature DB >> 26933831

Highly Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to Simple Aryl Ketones: Efficient Synthesis of Escitalopram.

Linwei Huang1, Jinbin Zhu1, Guangjun Jiao2, Zheng Wang3, Xingxin Yu1, Wei-Ping Deng4, Wenjun Tang5,6.   

Abstract

Highly enantioselective additions of arylboroxines to simple aryl ketones have been achieved for the first time with a Rh/(R,R,R,R)-WingPhos catalyst, thus providing a range of chiral diaryl alkyl carbinols with excellent ee values and yields. (R,R,R,R)-WingPhos has been proven to be crucial for the high reactivity and enantioselectivity. The method has enabled a new, concise, and enantioselective synthesis of the antidepressant drug escitalopram.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; enantioselectivity; ligand design; rhodium; total synthesis

Mesh:

Substances:

Year:  2016        PMID: 26933831     DOI: 10.1002/anie.201600979

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


  4 in total

1.  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

2.  Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands.

Authors:  Rui Miao; Yanping Xia; Yifei Wei; Lu Ouyang; Renshi Luo
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

3.  Asymmetric addition of Grignard reagents to ketones: culmination of the ligand-mediated methodology allows modular construction of chiral tertiary alcohols.

Authors:  Claudio Monasterolo; Ryan O'Gara; Saranna E Kavanagh; Sadbh E Byrne; Bartosz Bieszczad; Orla Murray; Michael Wiesinger; Rebecca A Lynch; Kirill Nikitin; Declan G Gilheany
Journal:  Chem Sci       Date:  2022-04-20       Impact factor: 9.969

4.  An Entry to Enantioenriched 3,3-Disubstituted Phthalides through Asymmetric Phase-Transfer-Catalyzed γ-Alkylation.

Authors:  Marina Sicignano; Rosaria Schettini; Giovanni Pierri; Maria Leda Marino; Irene Izzo; Francesco De Riccardis; Luca Bernardi; Giorgio Della Sala
Journal:  J Org Chem       Date:  2020-05-27       Impact factor: 4.354

  4 in total

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