A general synthesis of 2-alkoxy-2-phenylpropanoic acids

Monk, Keith A.; Duncan, Nathan C.; Bauch, Eric A.; Garner, Charles M.

doi:10.1016/j.tet.2008.06.105

Tetrahedron

2008

DOI: 10.1016/j.tet.2008.06.105

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A general synthesis of 2-alkoxy-2-phenylpropanoic acids

Keith A. Monk

Nathan C. Duncan

Eric A. Bauch

et al.

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Cited by 7 publications

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“…[12] When 4 am and 4 hm were treated with Mo(CO) 6 in a mixed solvent (H 2 O/ CH 3 CN) under refluxing conditions, α-alkoxy amides (7 am and 7 hm) were obtained in good yields (84% and 79%, respectively) by cleavage of the NÀ O bond. [13] In addition, hydrogenation with Pd/C of α-alkoxy amides (7 am and 7 hm) was realized to furnish biologically important α-hydroxy amides (8 am and 8 hm). [14] In conclusion, we have developed a metal and catalyst-free mild nucleophilic alkoxylation reaction of alcohols with in-situ generated azaoxyallyl cation from α-halohydroxamates.…”

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confidence: 99%

Metal‐free Nucleophilic Alkoxylation of in Situ‐Generated Azaoxyallyl Cations: Synthesis of Hindered Dialkyl Ether Derivatives

Son

Kim

2020

Asian J Org Chem

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A metal and catalyst-free, environmentally friendly synthesis of hindered dialkyl ether derivatives has been established via the nucleophilic alkoxylation of alcohols and α-halohydroxamates. The reactions of a variety of primary and secondary alcohols with azaoxyallyl cations generated in situ from α-halohydroxamates afforded a wide range of hindered dialkyl ether derivatives in good yields. Moreover, methods for the synthesis of α-alkoxyhydroxamic acids, α-alkoxy amides, and α-hydroxy amides from αalkoxy hydroxamates were established. [a] E. Scheme 1. Representative examples of hindered dialkyl ether synthesis. Scheme 2. Nucleophilic amination and alkoxylation of α-bromohydroxamate.

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confidence: 99%

Metal‐free Nucleophilic Alkoxylation of in Situ‐Generated Azaoxyallyl Cations: Synthesis of Hindered Dialkyl Ether Derivatives

Son

Kim

2020

Asian J Org Chem

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ChemInform Abstract: A General Synthesis of 2‐Alkoxy‐2‐phenylpropanoic Acids.

et al. 2008

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Hydroxycarboxylic acids (ether carboxylic acids) and esters Q 0450A General Synthesis of 2-Alkoxy-2-phenylpropanoic Acids. -The treatment of α-methylstyrene by MCPBA in a variety of alcohols affords propanols (III) via an acid-catalyzed in situ ring opening of the intermediate epoxide ring. The alcohols are oxidized to the acids. In the case of (IIIg), the ether is cleared and atrolactic acid (V) is formed. -(MONK, K. A.; DUNCAN, N. C.; BAUCH, E. A.; GARNER*, C. M.; Tetrahedron 64 (2008) 37, 8605-8609; Dep. Chem. Biochem., Baylor Univ., Waco, TX 76798, USA; Eng.) -Klein 52-083

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l-Threonine-catalysed asymmetric α-hydroxymethylation of cyclohexanone: application to the synthesis of pharmaceutical compounds and natural products

Chen

Chiang

et al. 2010

Tetrahedron

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A general synthesis of 2-alkoxy-2-phenylpropanoic acids

Cited by 7 publications

References 24 publications

Metal‐free Nucleophilic Alkoxylation of in Situ‐Generated Azaoxyallyl Cations: Synthesis of Hindered Dialkyl Ether Derivatives

Metal‐free Nucleophilic Alkoxylation of in Situ‐Generated Azaoxyallyl Cations: Synthesis of Hindered Dialkyl Ether Derivatives

ChemInform Abstract: A General Synthesis of 2‐Alkoxy‐2‐phenylpropanoic Acids.

l-Threonine-catalysed asymmetric α-hydroxymethylation of cyclohexanone: application to the synthesis of pharmaceutical compounds and natural products

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