Literature DB >> 15827627

A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions.

Kristian Rahbek Knudsen1, Karl Anker Jorgensen.   

Abstract

An approach to asymmetric catalysis based on chiral molecular recognition by the combination of chiral Lewis acids and chiral organocatalysis for the formation of optically active quarternary centers in the aza-Henry reaction is presented; this procedure leads to products with up to 98% ee and a diastereomeric ratio of 14 : 1 in excellent yields with catalyst loadings of 5 mol%.

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Year:  2005        PMID: 15827627     DOI: 10.1039/b500618j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  8 in total

1.  A Novel Bis-Thiourea Organocatalyst for the Asymmetric Aza-Henry Reaction.

Authors:  Constantinos Rampalakos; William D Wulff
Journal:  Adv Synth Catal       Date:  2008-08-04       Impact factor: 5.837

2.  Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

Authors:  Hua Yang; Rich G Carter
Journal:  Synlett       Date:  2010-09-01       Impact factor: 2.454

3.  Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor.

Authors:  Tyler A Davis; Michael W Danneman; Jeffrey N Johnston
Journal:  Chem Commun (Camb)       Date:  2012-04-30       Impact factor: 6.222

4.  Bifunctional asymmetric catalysis: amplification of Brønsted basicity can orthogonally increase the reactivity of a chiral Brønsted acid.

Authors:  Tyler A Davis; Jeremy C Wilt; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

5.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

6.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

7.  Enantioselective synthesis of α-quaternary Mannich adducts by palladium-catalyzed allylic alkylation: total synthesis of (+)-sibirinine.

Authors:  Yoshitaka Numajiri; Beau P Pritchett; Koji Chiyoda; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2015-01-20       Impact factor: 15.419

8.  Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution.

Authors:  Daniel J Sprague; Anand Singh; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825

  8 in total

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