Highly Stereoselective Chemoenzymatic Synthesis of the 3 H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

J Mangas-Sánchez, E Busto, V Gotor-Fernández…

Index: Mangas-Sanchez, Juan; Busto, Eduardo; Gotor-Fernandez, Vicente; Gotor, Vicente Organic Letters, 2012 , vol. 14, # 6 p. 1444 - 1447

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Citation Number: 17

Abstract

A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found to be the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous ...

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1-(2-AMINO-3-METHYLPHENYL)-ETHANONE Structure

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2-Amino-4-methy...

~78%

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122710-21-8

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2-Amino-5-fluorobenzoic acid Structure

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2-Amino-5-fluor...

METHYLLITHIUM Structure

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METHYLLITHIUM

~42%

1-(2-amino-4-fluorophenyl)ethanone Structure

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3-methyl-2-benzofuran-1(3H)-imine Structure

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3-methyl-2-benz...

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2-Acetylbenzonitrile Structure

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2-Acetylbenzonitrile

~%

3-Methyl-1,3-dihydro-2-benzofuran-1-one Structure

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3-Methyl-1,3-di...

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2'-Aminoacetophenone

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1363508-16-0

(S)-2-(1-hydrox...

~10%

1(3H)-Isobenzofuranone,3-methyl-,(3R)-(9CI) Structure

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1(3H)-Isobenzof...

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1-(2-Amino-4-methoxyphenyl)ethanone Structure

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1-(2-Amino-4-me...


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