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Dynamic Enzymatic Kinetic Resolution of Methyl 2,3-Dihydro-1H-indene-1-carboxylate

✍ Scribed by Jörg Pietruszka; Robert Christian Simon; Fabian Kruska; Manfred Braun

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
330 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A new reaction setup for kinetic enzymatic resolution was established and is demonstrated for the case of the hydrolase‐catalysed conversion of methyl 2,3‐dihydro‐1__H__‐indene‐1‐carboxylate (1) in conjunction with a base‐catalysed racemisation. The system allows controlled racemisation, resulting in efficient dynamic kinetic resolution (DKR) of the title compound. Short reaction times and high enantioselectivities were obtained with CAL‐B and TBD (1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene). Compound (R)‐1 (ee 95 %) served as a starting material in a domino reaction that led to the biaryl indanyl ketone (R)‐8, a lead compound for novel inhibitors of peptidyl‐prolyl‐cis/trans‐isomerases, in 94 % ee. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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## Abstract ^1^H, ^13^C and two‐dimensional NMR analyses were applied to determine the NMR parameters of 6‐(2′,3′‐dihydro‐1′__H__‐inden‐1′‐yl)‐1__H__‐indene. The measurements were accomplished with 0.5 mg of the substance, this quantity being sufficient to determine the chemical shifts of all the H