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Literature DB >> 20527773

Catalytic asymmetric transacetalization.

Ilija Corić¹, Sreekumar Vellalath, Benjamin List.

Abstract

A catalytic enantioselective transacetalization has been developed. The chiral phosphoric acid TRIP was demonstrated to be an efficient and highly enantioselective catalyst for the activation of O,O-acetals. The reaction enables the asymmetric synthesis of acetals with the acetal carbon as the only stereogenic center.

Entities: Chemical Gene

Mesh：

Substances：
Acetals

Year: 2010 PMID： 20527773 DOI： 10.1021/ja102753d

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

1. An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors: David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal: J Am Chem Soc Date: 2012-08-07 Impact factor: 15.419

2. 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

3. Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors: Ilija Čorić; Benjamin List
Journal: Nature Date: 2012-03-14 Impact factor: 49.962

4. The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors: Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal: Nat Chem Date: 2012-07-24 Impact factor: 24.427

5. Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors: Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2017-12-12 Impact factor: 15.336

6. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2012-06-25 Impact factor: 15.419

Catalytic asymmetric transacetalization.

1. An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

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

3. Asymmetric spiroacetalization catalysed by confined Brønsted acids.

4. The progression of chiral anions from concepts to applications in asymmetric catalysis.

5. Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

6. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

7. Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.

8. Controlling Enantioselectivity in Additions to Cyclic Oxocarbenium Ions via Transition Metal Catalysis.

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

10. Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.