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Literature DB >> 23744744

Shedding light on organocatalysis-light-assisted asymmetric ion-pair catalysis for the enantioselective hydrogenation of pyrylium ions.

Chien-Chi Hsiao¹, Hsuan-Hung Liao, Erli Sugiono, Iuliana Atodiresei, Magnus Rueping.

Abstract

A new light-driven asymmetric ion-pair catalysis procedure for the metal-free enantioselective hydrogenation of in situ generated pyrylium ions from readily available chalcones was developed (see scheme). The photo-assisted Brønsted acid catalyzed procedure has broad scope and allows, for the first time, access to valuable 4H-chromenes in good yields and with excellent enantioselectivities.

Entities: Chemical

Keywords: asymmetric catalysis; benzopyrane; chiral ion pair; oxocarbenium ion; reduction

Year: 2013 PMID： 23744744 DOI： 10.1002/chem.201300766

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

Keyword Cloud
Cited

8 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. Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Authors: Zhenyu Yang; Ying He; F Dean Toste
Journal: J Am Chem Soc Date: 2016-07-29 Impact factor: 15.419

3. 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

8. A mild, diastereoselective construction of cyclic and spirocyclic ketals employing a tandem photoisomerization/cyclization tactic.

Authors: Bo Li; Brett D Williams; Amos B Smith
Journal: Org Lett Date: 2014-12-09 Impact factor: 6.005

8 in total

Shedding light on organocatalysis-light-assisted asymmetric ion-pair catalysis for the enantioselective hydrogenation of pyrylium ions.

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

2. Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

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

4. Stereocontrolled cyanohydrin ether synthesis through chiral Brønsted acid-mediated vinyl ether hydrocyanation.

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

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

7. Decrypting Transition States by Light: Photoisomerization as a Mechanistic Tool in Brønsted Acid Catalysis.

8. A mild, diastereoselective construction of cyclic and spirocyclic ketals employing a tandem photoisomerization/cyclization tactic.