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Literature DB >> 21087021

Kinetic resolution of homoaldols via catalytic asymmetric transacetalization.

Ilija Čorić¹, Steffen Müller, Benjamin List.

Abstract

The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.

Entities: Chemical

Year: 2010 PMID： 21087021 DOI： 10.1021/ja108642s

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

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Cited

21 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

10. A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

Authors: Jeffrey Wu; Yi-Ming Wang; Amela Drljevic; Vivek Rauniyar; Robert J Phipps; F Dean Toste
Journal: Proc Natl Acad Sci U S A Date: 2013-08-06 Impact factor: 11.205

Kinetic resolution of homoaldols via 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. Chiral Brønsted Acid Catalyzed Kinetic Resolutions.

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

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

Review 7. Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

8. Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases.

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

10. A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.