Literature DB >> 20718476

Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.

Graeme Barker1, Peter O'Brien, Kevin R Campos.   

Abstract

A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered a range of functionalized pyrrolidines, imidazolidines, and piperazines in 43-83% yield.

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Year:  2010        PMID： 20718476     DOI： 10.1021/ol1017799

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Total synthesis of lepadiformine alkaloids using N-Boc α-amino nitriles as trianion synthons.

Authors:  Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

2.  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

3.  Targeting tumor hypoxia with 2-nitroimidazole-indocyanine green dye conjugates.

Authors:  Yan Xu; Saeid Zanganeh; Innus Mohammad; Andres Aguirre; Tianheng Wang; Yi Yang; Liisa Kuhn; Michael B Smith; Quing Zhu
Journal:  J Biomed Opt       Date:  2013-06       Impact factor: 3.170

4.  Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway.

Authors:  Christopher K Prier; David W C MacMillan
Journal:  Chem Sci       Date:  2014-11       Impact factor: 9.825

5.  Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides.

Authors:  Timothy K Beng; Sidney M Wilkerson-Hill; Richmond Sarpong
Journal:  Org Lett       Date:  2014-01-23       Impact factor: 6.005

6.  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

Review 7.  Opportunities and challenges for direct C-H functionalization of piperazines.

Authors:  Zhishi Ye; Kristen E Gettys; Mingji Dai
Journal:  Beilstein J Org Chem       Date:  2016-04-13       Impact factor: 2.883
  7 in total

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