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Dynamic Enzymatic Kinetic Resolution of Methyl 2,3‐Dihydro‐1 H ‐indene‐1‐carboxylate
Author(s) -
Pietruszka Jörg,
Simon Robert Christian,
Kruska Fabian,
Braun Manfred
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901025
Subject(s) - chemistry , kinetic resolution , indene , carboxylate , stereochemistry , ketone , enzyme , kinetic energy , methyl vinyl ketone , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis , physics , quantum mechanics
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)