Literature DB >> 25386099

Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.

Junbin Han, Zhichao Lu, Gerald B Hammond, Bo Xu.   

Abstract

Starting from a primary amine-tethered alkyne 1, a copper-catalyzed three-component tandem amination/cyanation/alkylation sequence gives α-CN pyrrolidine 6 in good yield and regioselectivity. Also, a silver mediated tandem amination/oxidation of a secondary amine-tethered alkyne 7 produces functionalized pyrrole 8 in good yield. All reactions were conducted in one pot without any protection/deprotection steps.

Entities:  

Keywords:  amination; cyanation; pyrroles; pyrrolidines; tandem

Year:  2014        PMID： 25386099      PMCID： PMC4224302          DOI： 10.1002/ejoc.201402748

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  15 in total

1.  Rare-earth metal triflates in organic synthesis.

Authors:  Shū Kobayashi; Masaharu Sugiura; Hidetoshi Kitagawa; William W-L Lam
Journal:  Chem Rev       Date:  2002-06       Impact factor: 60.622

2.  Alpha-amination of nitrogen heterocycles: ring-fused aminals.

Authors:  Chen Zhang; Chandra Kanta De; Rudrajit Mal; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

Review 3.  Coinage metal-assisted synthesis of heterocycles.

Authors:  Nitin T Patil; Yoshinori Yamamoto
Journal:  Chem Rev       Date:  2008-07-09       Impact factor: 60.622

4.  Organocatalytic approach to benzofused nitrogen-containing heterocycles: enantioselective total synthesis of (+)-angustureine.

Authors:  Santos Fustero; Javier Moscardó; Diego Jiménez; María Dolores Pérez-Carrión; María Sánchez-Roselló; Carlos Del Pozo
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  Synthesis of Cyclic α-Aminophosphonates through Copper Catalyzed Enamine Activation.

Authors:  Junbin Han; Robert S Paton; Bo Xu; Gerald B Hammond
Journal:  Synthesis (Stuttg)       Date:  2013-02-01       Impact factor: 3.157

6.  Copper/DIPEA-catalyzed, aldehyde-induced tandem decarboxylation-coupling of natural α-amino acids and phosphites or secondary phosphine oxides.

Authors:  Dongxu Yang; Depeng Zhao; Lijuan Mao; Linqing Wang; Rui Wang
Journal:  J Org Chem       Date:  2011-07-06       Impact factor: 4.354

7.  Highly efficient and regioselective platinum(II)-catalyzed tandem synthesis of multiply substituted indolines and tetrahydroquinolines.

Authors:  Xin-Yuan Liu; Chi-Ming Che
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Highly efficient Cu(I)-catalyzed synthesis of N-heterocycles through a cyclization-triggered addition of alkynes.

Authors:  Junbin Han; Bo Xu; Gerald B Hammond
Journal:  J Am Chem Soc       Date:  2010-01-27       Impact factor: 15.419

9.  A ruthenium-catalyzed, atom-economical synthesis of nitrogen heterocycles.

Authors:  Barry M Trost; Nuno Maulide; Robert C Livingston
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

Review 10.  Stereoselectively fluorinated N-heterocycles: a brief survey.

Authors:  Xiang-Guo Hu; Luke Hunter
Journal:  Beilstein J Org Chem       Date:  2013-11-29       Impact factor: 2.883
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