The Journal of organic chemistry

Grubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α, β-unsaturated Esters

RN Nair, TD Bannister

Index: Nair, Reji N.; Bannister, Thomas D. Journal of Organic Chemistry, 2014 , vol. 79, # 3 p. 1467 - 1472

Full Text: HTML

Citation Number: 10

Abstract

A direct and scalable route to γ-keto-α, β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2° allylic alcohols. The metathesis step is followed by oxidation to give the desired products in high yield on scales of up to 25 g.

Related Articles:

Grubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α, β-unsaturated Esters

[Schmidt, Bernd; Hauke, Sylvia Organic and Biomolecular Chemistry, 2013 , vol. 11, # 25 p. 4194 - 4206]

Aromatic sulfide inhibitors of histone deacetylase based on arylsulfinyl-2, 4-hexadienoic acid hydroxyamides

[Cass, Quezia B.; Jaxa-Chamiec, Albert A.; Kunec, Ellen K.; Sammes, Peter G. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 11 p. 2683 - 2686]

Preparation and rearrangement of some conjugated phenylsulphinylacetate derivatives

[Cass, Quezia B.; Jaxa-Chamiec, Albert A.; Sammes, Peter G. Journal of the Chemical Society, Chemical Communications, 1981 , # 24 p. 1248 - 1250]

Aromatic sulfide inhibitors of histone deacetylase based on arylsulfinyl-2, 4-hexadienoic acid hydroxyamides

[Cass, Quezia B.; Jaxa-Chamiec, Albert A.; Kunec, Ellen K.; Sammes, Peter G. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 11 p. 2683 - 2686]

Aromatic sulfide inhibitors of histone deacetylase based on arylsulfinyl-2, 4-hexadienoic acid hydroxyamides

[Cass, Quezia B.; Jaxa-Chamiec, Albert A.; Kunec, Ellen K.; Sammes, Peter G. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 11 p. 2683 - 2686]

More Articles...