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Literature DB >> 21033718

Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides.

Matthew M Coulter¹, Kevin G M Kou, Baye Galligan, Vy M Dong.

Abstract

We report a Rh-catalyzed, regio- and enantioselective intermolecular olefin hydroacylation under mild conditions. Hydroacylations between homoallylic sulfides, containing a substrate-bound directing group, and salicylaldehyde derivatives occur in the presence of a spiro-phosphoramidite ligand, (R)-SIPHOS-PE, to give α-branched ketones in >20:1 selectivity and up to 97% ee. Our conditions are also applicable to the asymmetric intermolecular hydroacylation of 1,2-disubstituted olefins.

Entities: Chemical

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Year: 2010 PMID： 21033718 DOI： 10.1021/ja107198e

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

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Cited

24 in total

1. Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex.

Authors: Junghwa Kim; Chae S Yi
Journal: ACS Catal Date: 2016-04-19 Impact factor: 13.084

2. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors: Andrew M Harned
Journal: Tetrahedron Lett Date: 2014-08-20 Impact factor: 2.415

3. Enantioselective hydroacylation of olefins with rhodium catalysts.

Authors: Stephen K Murphy; Vy M Dong
Journal: Chem Commun (Camb) Date: 2014-11-18 Impact factor: 6.222

4. Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.

Authors: Xiang-Wei Du; Levi M Stanley
Journal: Org Lett Date: 2015-06-22 Impact factor: 6.005

10. α- and β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- and Enantioselectivity in Hydroacylation of 1,3-Dienes.

Authors: Mahesh M Parsutkar; T V RajanBabu
Journal: J Am Chem Soc Date: 2021-08-05 Impact factor: 15.419

Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides.

1. Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex.

2. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

3. Enantioselective hydroacylation of olefins with rhodium catalysts.

4. Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.

5. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

6. Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.

7. Substrate-directed hydroacylation: rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes.

Review 8. Teaching Aldehydes New Tricks Using Rhodium- and Cobalt-Hydride Catalysis.

9. Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

10. α- and β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- and Enantioselectivity in Hydroacylation of 1,3-Dienes.