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Issue 8, 2012
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Enantiopure 3-methyl-3,4-dihydroisocoumarins and 3-methyl-1,2,3,4-tetrahydroisoquinolines via chemoenzymatic asymmetric transformations

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Abstract

A new divergent and asymmetric synthetic route has been developed for the production of enantiomerically pure isocoumarin and isoquinoline derivatives. Stereoselective formation of 2-(2-hydroxypropyl)benzonitriles has been identified as the key step. Rhizomucor miehei lipase has displayed from moderate to excellent selectivities in the acetylation of its (R)-enantiomers, while ADH-A from Rhodococcus ruber catalyzed the bioreduction of the corresponding ketones with excellent activities and stereopreferences. Enantiopure alcohols obtained in this manner have been used for the straightforward synthesis of a series of 3-methyl-3,4-dihydroisocoumarins and 3-methyl-1,2,3,4-tetrahydroisoquinolines with good overall yields.

Graphical abstract: Enantiopure 3-methyl-3,4-dihydroisocoumarins and 3-methyl-1,2,3,4-tetrahydroisoquinolines via chemoenzymatic asymmetric transformations

  • This article is part of the themed collection: Biocatalysis
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Publication details

The article was received on 14 Feb 2012, accepted on 20 Apr 2012 and first published on 24 Apr 2012


Article type: Paper
DOI: 10.1039/C2CY20152F
Catal. Sci. Technol., 2012,2, 1590-1595

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    Enantiopure 3-methyl-3,4-dihydroisocoumarins and 3-methyl-1,2,3,4-tetrahydroisoquinolines via chemoenzymatic asymmetric transformations

    J. Mangas-Sánchez, E. Busto, V. Gotor-Fernández and V. Gotor, Catal. Sci. Technol., 2012, 2, 1590
    DOI: 10.1039/C2CY20152F

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