Literature DB >> 20235261

Lithiation-electrophilic substitution of N-thiopivaloylazetidine.

David M Hodgson1, Johannes Kloesges.   

Abstract

The fourth protocol: the rarely studied N-thiopivaloyl group plays a crucial role in mediating efficient α lithiation and incorporation of diverse electrophiles onto an azetidine ring; in the presence of chiral ligands, this chemistry also provides the first example of an enantioselective electrophilic substitution on a four-membered ring.
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2010        PMID: 20235261     DOI: 10.1002/anie.201000058

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


  6 in total

1.  Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors:  Anh T Tran; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-24       Impact factor: 15.336

2.  Dynamic Phenomena and Complexation Effects in the α-Lithiation and Asymmetric Functionalization of Azetidines.

Authors:  Pantaleo Musci; Marco Colella; Angela Altomare; Giuseppe Romanazzi; Nadeem S Sheikh; Leonardo Degennaro; Renzo Luisi
Journal:  Molecules       Date:  2022-04-29       Impact factor: 4.927

3.  Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles.

Authors:  Pritha Verma; Jeremy M Richter; Nikita Chekshin; Jennifer X Qiao; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-03-09       Impact factor: 15.419

4.  α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors:  Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-09-10       Impact factor: 15.419

5.  Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.

Authors:  David M Hodgson; Christopher I Pearson; Madiha Kazmi
Journal:  Org Lett       Date:  2014-01-10       Impact factor: 6.005

6.  Enantioselective amine α-functionalization via palladium-catalysed C-H arylation of thioamides.

Authors:  Pankaj Jain; Pritha Verma; Guoqin Xia; Jin-Quan Yu
Journal:  Nat Chem       Date:  2016-10-03       Impact factor: 24.427

  6 in total

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