Synthesis of a new insoluble polymer-supported chiral alcohol auxiliary and its first application to nucleophilic addition to ketenes

R Akkari, M Calmes, N Mai, M Rolland…

Index: Akkari; Calmes; Mai; Rolland; Martinez Journal of Organic Chemistry, 2001 , vol. 66, # 17 p. 5859 - 5865

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Citation Number: 33

Abstract

The preparation of a new optically active alcohol with a carboxylic function that allowed its attachment to an amine-functionalized insoluble polymer is described. Its first use as a polymer supported chiral auxiliary is demonstrated by asymmetric transformation of two racemic aryl propionic acids via ketene formation (95-96% ee).

 Related Synthetic Route
2-(4-isobutylphenyl)-propionic acid chloride Structure

71381-91-4

2-(4-isobutylph...

~%

(S)-(+)-Ibuprofen Structure

51146-56-6

(S)-(+)-Ibuprofen

(R)-(-)-Ibuprofen Structure

51146-57-7

(R)-(-)-Ibuprofen

N/A Structure

362470-63-1

N/A

~99%

ketoprofen Structure

22071-15-4

ketoprofen

2-(4-isobutylphenyl)-propionic acid chloride Structure

71381-91-4

2-(4-isobutylph...

~%

(S)-(+)-Ibuprofen Structure

51146-56-6

(S)-(+)-Ibuprofen

(R)-(-)-Ibuprofen Structure

51146-57-7

(R)-(-)-Ibuprofen


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