Literature DB >> 17078687

Substrate-directed stereoselectivity in vicinal diamine-catalyzed synthesis of warfarin.

Hyunwoo Kim1, Cindy Yen, Philippa Preston, Jik Chin.   

Abstract

[Structure: see text] A new mechanism involving a diimine intermediate is proposed for vicinal diamine-catalyzed synthesis of warfarin. Decreasing the NCCN dihedral angle by varying the diamine results in an increase in the enantioselectivity of warfarin synthesis.

Entities:  

Year:  2006        PMID： 17078687     DOI： 10.1021/ol062000v

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


  10 in total

1.  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

2.  Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.

Authors:  Pauline Peltier-Pain; Shannon C Timmons; Agnès Grandemange; Etienne Benoit; Jon S Thorson
Journal:  ChemMedChem       Date:  2011-06-28       Impact factor: 3.466

3.  Multiple UDP-glucuronosyltransferases in human liver microsomes glucuronidate both R- and S-7-hydroxywarfarin into two metabolites.

Authors:  C Preston Pugh; Dakota L Pouncey; Jessica H Hartman; Robert Nshimiyimana; Linda P Desrochers; Thomas E Goodwin; Gunnar Boysen; Grover P Miller
Journal:  Arch Biochem Biophys       Date:  2014-10-19       Impact factor: 4.013

4.  Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

5.  Stereospecific Metabolism of R- and S-Warfarin by Human Hepatic Cytosolic Reductases.

Authors:  Dustyn A Barnette; Bryce P Johnson; Dakota L Pouncey; Robert Nshimiyimana; Linda P Desrochers; Thomas E Goodwin; Grover P Miller
Journal:  Drug Metab Dispos       Date:  2017-06-23       Impact factor: 3.922

6.  Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine.

Authors:  Wei Wang; Ling Ye; Zhichuan Shi; Zhigang Zhao; Xuefeng Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

7.  Adaptation of a small-molecule hydrogen-bond donor catalyst to an enantioselective hetero-Diels-Alder reaction hypothesized for brevianamide biosynthesis.

Authors:  Daniel J Sprague; Benjamin M Nugent; Ryan A Yoder; Brandon A Vara; Jeffrey N Johnston
Journal:  Org Lett       Date:  2015-01-31       Impact factor: 6.005

8.  Combining silver catalysis and organocatalysis: a sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins.

Authors:  Daniel Hack; Pankaj Chauhan; Kristina Deckers; Gary N Hermann; Lucas Mertens; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-09-24       Impact factor: 6.005

9.  Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts.

Authors:  Qingqing Wang; Wei Wang; Ling Ye; Xuejun Yang; Xinying Li; Zhigang Zhao; Xuefeng Li
Journal:  Molecules       Date:  2017-06-30       Impact factor: 4.411

Review 10.  Asymmetric organocatalysis at the service of medicinal chemistry.

Authors:  Alfredo Ricci
Journal:  ISRN Org Chem       Date:  2014-03-11
  10 in total

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