Literature DB >> 22913599

Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

Magnus Rueping1, Chandra M R Volla, Iuliana Atodiresei.   

Abstract

A synergistic catalytic system for the first asymmetric addition of aldehydes to in situ generated prochiral oxocarbenium ions has been developed. The dual catalytic protocol allows the simultaneous activation of both electrophile and nucleophile and provides access to a variety of valuable chiral 2H-chromenes with excellent enantioselectivities.

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Year:  2012        PMID： 22913599     DOI： 10.1021/ol302084q

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


  10 in total

1.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors:  Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal:  J Org Chem       Date:  2015-04-07       Impact factor: 4.354

2.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

3.  Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Authors:  Yi Luan; Yue Qi; Hongyi Gao; Qianqian Ma; Scott E Schaus
Journal:  European J Org Chem       Date:  2014-11-01

4.  Enantioselective synthesis of 1,2-dihydronaphthalene-1-carbaldehydes by addition of boronates to isochromene acetals catalyzed by tartaric acid.

Authors:  Yi Luan; Keith S Barbato; Philip N Moquist; Tomohiro Kodama; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

5.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

6.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

7.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

8.  Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.

Authors:  Fei Yang; Yangshan Li; Paul E Floreancig; Xiaoyan Li; Lei Liu
Journal:  Org Biomol Chem       Date:  2018-07-18       Impact factor: 3.876

9.  Helical Multi-Coordination Anion-Binding Catalysts for the Highly Enantioselective Dearomatization of Pyrylium Derivatives.

Authors:  Theresa Fischer; Julia Bamberger; Melania Gómez-Martínez; Dariusz G Piekarski; Olga García Mancheño
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-13       Impact factor: 15.336

10.  Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives.

Authors:  Gang Wang; Xiaodong Xin; Zehua Wang; Gang Lu; Yudao Ma; Lei Liu
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919
  10 in total

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