Literature DB >> 14961639

Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst.

Tomotaka Okino1, Satoru Nakamura, Tomihiro Furukawa, Yoshiji Takemoto.   

Abstract

[reaction: see text] The aza-Henry reaction of imines with nitroalkanes was promoted by chiral thiourea with an N,N-dimethylamino group to give beta-nitroamines with good enantioselectivity. Various N-protected imines were examined as substrates. N-Phosphinoylimine gave the best result in terms of chemical yield and enantioselectivity (up to 91% yield, up to 76% ee).

Entities:  

Year:  2004        PMID: 14961639     DOI: 10.1021/ol0364531

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


  22 in total

1.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors:  Hongming Li; Baomin Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

2.  Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Authors:  Douglas E Fuerst; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

3.  Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst.

Authors:  Joseph A Izzo; Yaroslaw Myshchuk; Jennifer S Hirschi; Mathew J Vetticatt
Journal:  Org Biomol Chem       Date:  2019-04-17       Impact factor: 3.876

4.  Catalytic, Enantioselective Synthesis of Stilbene cis-Diamines: A Concise Preparation of (-)-Nutlin-3, a Potent p53/MDM2 Inhibitor.

Authors:  Tyler A Davis; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2011-03-25       Impact factor: 9.825

5.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

6.  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

7.  The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acids.

Authors:  Jun Song; Yi Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

8.  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

9.  Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.

Authors:  Brandon A Vara; Anand Mayasundari; John C Tellis; Michael W Danneman; Vanessa Arredondo; Tyler A Davis; Jaeki Min; Kristin Finch; R Kiplin Guy; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

10.  Covalent Poly(lactic acid) Nanoparticles for the Sustained Delivery of Naloxone.

Authors:  Andrew J Kassick; Heather N Allen; Saigopalakrishna S Yerneni; Fathima Pary; Marina Kovaliov; Cooper Cheng; Marco Pravetoni; Nestor D Tomycz; Donald M Whiting; Toby L Nelson; Michael Feasel; Phil G Campbell; Benedict Kolber; Saadyah Averick
Journal:  ACS Appl Bio Mater       Date:  2019-07-25
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