Literature DB >> 19655732

Asymmetric aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B.

Takahiko Itoh1, Hayato Ishikawa, Yujiro Hayashi.   

Abstract

The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hydroxyindole alkaloids. Short syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B have been accomplished.

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Year:  2009        PMID: 19655732     DOI: 10.1021/ol901432a

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


  13 in total

1.  Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.

Authors:  Qunsheng Guo; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors:  Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

3.  Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Authors:  Sandun Perera; Vijaya Kumar Naganaboina; Long Wang; Bin Zhang; Qunsheng Guo; Laxmidhar Rout; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-06-30       Impact factor: 5.837

4.  Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.

Authors:  Max Moskowitz; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336

5.  Highly enantioselective catalytic benzoyloxylation of 3-aryloxindoles using chiral VAPOL calcium phosphate.

Authors:  Zuhui Zhang; Wenhua Zheng; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-22       Impact factor: 15.336

6.  Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.

Authors:  Elisa G Gutierrez; Casey J Wong; Aziza H Sahin; Annaliese K Franz
Journal:  Org Lett       Date:  2011-10-11       Impact factor: 6.005

7.  Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

Authors:  Jie Guang; Qunsheng Guo; John Cong-Gui Zhao
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

8.  Asymmetric Aldol Reaction of 3-Acetyl-2H-chromen-2-ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst.

Authors:  Santhi Abbaraju; John Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

9.  5-Chloro-1-(4-meth-oxy-benz-yl)indoline-2,3-dione.

Authors:  Weiyao Wu; Tingting Zheng; Shengli Cao; Zhichang Xiao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-08

10.  Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols.

Authors:  Daniel L Silverio; Sebastian Torker; Tatiana Pilyugina; Erika M Vieira; Marc L Snapper; Fredrik Haeffner; Amir H Hoveyda
Journal:  Nature       Date:  2013-02-14       Impact factor: 49.962

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