Literature DB >> 24024961

Ring expansions of vinyloxiranes, -thiiranes, and -aziridines: synthetic approaches, challenges, and catalytic success stories.

Elizabeth A Ilardi1, Jon T Njardarson.   

Abstract

Ring expansion reactions of strained vinylic heterocyclic substrates have attracted the attention of the synthetic community for decades. Strategic manipulations of these organic architectures enable access to many useful synthetic intermediates. This paper highlights various methods for the ring expansion of vinyloxiranes, -thiiranes, and -aziridines described in the literature from 1964 to 2013.

Entities:  

Year:  2013        PMID: 24024961     DOI: 10.1021/jo401776s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

Review 1.  Synthesis of sulfur-containing heterocycles via ring enlargement.

Authors:  Bakr F Abdel-Wahab; Saad Shaaban; Gamal A El-Hiti
Journal:  Mol Divers       Date:  2018-01-31       Impact factor: 2.943

2.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

3.  Ni(II)-catalyzed asymmetric alkenylations of ketimines.

Authors:  Mao Quan; Xiaoxiao Wang; Liang Wu; Ilya D Gridnev; Guoqiang Yang; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919

4.  Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage.

Authors:  Yuting Liao; Xiaohua Liu; Yu Zhang; Yali Xu; Yong Xia; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-02-23       Impact factor: 9.825

5.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419

6.  Palladium-catalyzed regioselective and stereo-invertive ring-opening borylation of 2-arylaziridines with bis(pinacolato)diboron: experimental and computational studies.

Authors:  Youhei Takeda; Akinobu Kuroda; W M C Sameera; Keiji Morokuma; Satoshi Minakata
Journal:  Chem Sci       Date:  2016-06-09       Impact factor: 9.825

7.  Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.

Authors:  Josephine Eshon; Kate A Nicastri; Steven C Schmid; William T Raskopf; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  Nat Commun       Date:  2020-03-09       Impact factor: 14.919

  7 in total

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