Literature DB >> 15941248

An entry to a chiral dihydropyrazole scaffold: enantioselective [3 + 2] cycloaddition of nitrile imines.

Mukund P Sibi1, Levi M Stanley, Craig P Jasperse.   

Abstract

We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared.

Entities:  

Year:  2005        PMID： 15941248     DOI： 10.1021/ja051650b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid.

Authors:  J Caleb Hethcox; Charles S Shanahan; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

2.  Enantioselective Radical Reactions. Formation of Chiral Quaternary Centers.

Authors:  Mukund P Sibi; Liwen He
Journal:  Synlett       Date:  2006-03       Impact factor: 2.454

3.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

4.  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

5.  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

6.  Catalytic synthesis of nonracemic azaproline derivatives by cyclization of β-alkynyl hydrazines under kinetic resolution conditions.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-15       Impact factor: 15.336

7.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

8.  Environmentally Benign Lewis Acid Promoted [2+3]-Dipolar Cycloaddition Reactions of Nitrile Imines with Alkenes in Water.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  European J Org Chem       Date:  2013-11

9.  A Novel Synthesis of 1,3,5-Trisubstituted Pyrazoles through a Spiro-pyrazoline Intermediate via a Tandem 1,3-Dipolar Cycloaddition/Elimination.

Authors:  Sureshbabu Dadiboyena; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2009-01-21       Impact factor: 2.415

10.  Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

Authors:  Anthony L Gerten; Michael C Slade; Kelsie M Pugh; Levi M Stanley
Journal:  Org Biomol Chem       Date:  2013-10-17       Impact factor: 3.876
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