Literature DB >> 25302713

Intramolecular metalloamination of N,N-dimethylhydrazinoalkenes: a versatile method to access functionalized piperidines and pyrrolidines.

Bryce Sunsdahl1, Adrian R Smith, Tom Livinghouse.   

Abstract

Highly diastereoselective metalloamination/cyclization reactions of zinc(II) hydrazides obtained through reaction of diethylzinc with N,N-dimethylhydrazinoalkenes are described. The resulting organozinc intermediates undergo facile allylation and acylation, in situ, to provide the corresponding functionalized piperidines and pyrrolidines.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclization; hydrazines; metalloamination; nitrogen heterocycles; organozinc compounds

Year:  2014        PMID： 25302713     DOI： 10.1002/anie.201407768

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


  4 in total

1.  Diethylzinc-Mediated Metalloamination-Alkylation of N, N-Dimethylhydrazinoalkenes. Catalysis of C-Zn Alkylation Using Simple Cu(I) Salts.

Authors:  Ky Mickelsen; Sean Zabawa; Tom Livinghouse
Journal:  Synlett       Date:  2017-10-12       Impact factor: 2.454

2.  Copper(I)-Catalyzed Cross-Coupling of 1-Bromoalkynes with N-Heterocyclic Organozinc Reagents.

Authors:  Christian Frabitore; Jérome Lépeule; Tom Livinghouse
Journal:  Molecules       Date:  2022-07-17       Impact factor: 4.927

3.  Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect.

Authors:  Tuhin Patra; Peter Bellotti; Felix Strieth-Kalthoff; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-21       Impact factor: 15.336

Review 4.  Opportunities for Expanding Encoded Chemical Diversification and Improving Hit Enrichment in mRNA-Displayed Peptide Libraries.

Authors:  Paddy R A Melsen; Ryoji Yoshisada; Seino A K Jongkees
Journal:  Chembiochem       Date:  2022-02-18       Impact factor: 3.461
  4 in total

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