Literature DB >> 30411722

Conformationally Constrained Bis(oxazoline) Derived Chiral Catalyst : A Highly Effective Enantioselective Diels-Alder Reaction.

Arun K Ghosh1, Packiarajan Mathivanan1, John Cappiello1.   

Abstract

The reaction of cyclopentadiene with various bidentate dienophiles in the presence of 4-10 mol% of copper(II)-bis(oxazoline) complexes afforded excellent endo/exo selectivity as well as endo enantioselectivity (95-99% ee) and isolated yields. On the other hand, Diels-Alder reaction with Mg(II)-complexes afforded a modest ( 61% ee) reversal in enantioselectivity.

Entities:  

Year:  1996        PMID： 30411722      PMCID： PMC6219759          DOI： 10.1016/0040-4039(96)00721-6

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  4 in total

1.  STEREOSELECTIVE REDUCTION OF α-HYDROXY OXIME ETHERS: A CONVENIENT ROUTE TO CIS-1,2-AMINO ALCOHOLS.

Authors:  Arun K Ghosh; Sean P Mckee; Wilham M Sanders
Journal:  Tetrahedron Lett       Date:  2001-03-09       Impact factor: 2.415

2.  Highly Enantioselective Aldol Reaction: Development of a New Chiral Auxiliary from cis-1-Amino-2-hydroxyindan.

Authors:  Arun K Ghosh; Tien T Duong; Sean P McKee
Journal:  J Chem Soc Chem Commun       Date:  1992

3.  Chiral Auxiliary Mediated Conjugate Reduction and Asymmetric Protonation: Synthesis of High Affinity Ligands for HIV Protease Inhibitors.

Authors:  Arun K Ghosh; Wenming Liu
Journal:  J Org Chem       Date:  1995-09-01       Impact factor: 4.354

4.  ASYMMETRIC DIELS-ALDER REACTION : CIS-1-ARYLSULFONAMIDO-2-INDANOLS AS HIGHLY EFFECTIVE CHIRAL AUXILIARIES.

Authors:  Arun K Ghosh; Packiarajan Mathivanan
Journal:  Tetrahedron Asymmetry       Date:  1996-02
  4 in total
  3 in total

1.  C 2-Symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis.

Authors:  Arun K Ghosh; Packiarajan Mathivanan; John Cappiello
Journal:  Tetrahedron Asymmetry       Date:  1998-01-16

2.  Bis(oxazoline) derived cationic aqua complexes: highly effective catalysts for enantioselective Diels-Alder reactions.

Authors:  Arun K Ghosh; Hanna Cho; John Cappiello
Journal:  Tetrahedron Asymmetry       Date:  2000-06-15

Review 3.  Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

Authors:  Andrew F Zahrt; Soumitra V Athavale; Scott E Denmark
Journal:  Chem Rev       Date:  2019-12-30       Impact factor: 60.622
  3 in total

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