Literature DB >> 11150215

Versatile, diastereoselective additions of silyl ketene acetals, allyl tributylstannane, and Me(3)SiCN to N-acyl pyrazolines: asymmetric synthesis of densely functionalized pyrazolidines

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Abstract

We report the diastereoselective addition of a wide range of nucleophiles to chiral pyrazolines to provide facile access to a range of useful densely functionalized building blocks for asymmetric synthesis. Coupled with the asymmetric cycloaddition reaction of Me(3)SiCHN(2) to chiral acrylates, access to these chiral heterocycles is considerably expanded.

Entities:  

Year:  2000        PMID: 11150215     DOI: 10.1021/ol006873f

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


  5 in total

1.  Solution-phase parallel synthesis of a library of delta(2)-pyrazolines.

Authors:  Shankar Manyem; Mukund P Sibi; Gerald H Lushington; Benjamin Neuenswander; Frank Schoenen; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2007 Jan-Feb

2.  Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ2-pyrazolines.

Authors:  Nathaniel R Campbell; Bingfeng Sun; Ravi P Singh; Li Deng
Journal:  Adv Synth Catal       Date:  2011-11-01       Impact factor: 5.837

3.  Synthesis, receptor binding and activity of iso and azakainoids.

Authors:  Wentian Wang; Dragan D Simovic; Mingping Di; Lynne Fieber; Kathleen S Rein
Journal:  Bioorg Med Chem Lett       Date:  2013-02-16       Impact factor: 2.823

4.  Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.

Authors:  Natalie C Giampietro; John P Wolfe
Journal:  J Am Chem Soc       Date:  2008-09-06       Impact factor: 15.419

5.  Direct catalytic asymmetric synthesis of pyrazolidine derivatives.

Authors:  Luca Deiana; Gui-Ling Zhao; Hans Leijonmarck; Junliang Sun; Christian W Lehmann; Armando Córdova
Journal:  ChemistryOpen       Date:  2012-06-21       Impact factor: 2.911

  5 in total

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