Literature DB >> 24027174

A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation.

Marie-Kristin Lemke1, Pia Schwab, Petra Fischer, Sandra Tischer, Morris Witt, Laurence Noehringer, Victor Rogachev, Anne Jäger, Olga Kataeva, Roland Fröhlich, Peter Metz.   

Abstract

A surprisingly selective, non-enzymatic kinetic resolution of readily available, racemic β-chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p-toluenesulfonyl).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; flavonoids; glabrol; kinetic resolution; natural products

Mesh：

Substances：

Year:  2013        PMID： 24027174     DOI： 10.1002/anie.201306500

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity.

Authors:  Qingjing Yang; Zihao Wang; Catherine Hong Huan Hor; Haitao Xiao; Zhaoxiang Bian; Jun Joelle Wang
Journal:  Sci Adv       Date:  2022-06-03       Impact factor: 14.957

2.  Enantioselective Synthesis of Homoisoflavanones by Asymmetric Transfer Hydrogenation and Their Biological Evaluation for Antiangiogenic Activity.

Authors:  Myunghoe Heo; Bit Lee; Kamakshi Sishtla; Xiang Fei; Sanha Lee; Soojun Park; Yue Yuan; Seul Lee; Sangil Kwon; Jungeun Lee; Sanghee Kim; Timothy W Corson; Seung-Yong Seo
Journal:  J Org Chem       Date:  2019-08-05       Impact factor: 4.354

3.  Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.

Authors:  Steven D Stone; Neil J Lajkiewicz; Luke Whitesell; Ahmed Hilmy; John A Porco
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

4.  Easy To Synthesize, Robust Organo-osmium Asymmetric Transfer Hydrogenation Catalysts.

Authors:  James P C Coverdale; Carlos Sanchez-Cano; Guy J Clarkson; Rina Soni; Martin Wills; Peter J Sadler
Journal:  Chemistry       Date:  2015-04-08       Impact factor: 5.236

5.  Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications.

Authors:  Shekinah A Bass; Dynasty M Parker; Tania J Bellinger; Aireal S Eaton; Angelica S Dibble; Kaata L Koroma; Sylvia A Sekyi; David A Pollard; Fenghai Guo
Journal:  Molecules       Date:  2018-07-15       Impact factor: 4.411

6.  Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone.

Authors:  Tania J Bellinger; Teavian Harvin; Ti'Bran Pickens-Flynn; Nataleigh Austin; Samuel H Whitaker; Mai Ling C Tang Yuk Tutein; Dabria T Hukins; Nichele Deese; Fenghai Guo
Journal:  Molecules       Date:  2020-05-01       Impact factor: 4.411
  6 in total

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