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, 2010 , vol. 12, # 15 p. 3498 - 3501

Full Text: HTML

Citation Number: 18

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 ...

Related Articles:

New synthesis of 2-aryl-3-substituted benzo [b] furans from benzyl 2-halophenyl ethers

[Sanz, Roberto; Miguel, Delia; Martinez, Alberto; Perez, Antonio Journal of Organic Chemistry, 2006 , vol. 71, # 10 p. 4024 - 4027]

On the reactivity of o-lithioaryl ethers: tandem anion translocation and wittig rearrangement

[Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Marcos, Cesar; Trabada, Marta Organic Letters, 2002 , vol. 4, # 9 p. 1587 - 1590]

More Articles...