In:
European Journal of Organic Chemistry, Wiley, Vol. 2009, No. 35 ( 2009-12), p. 6217-6224
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)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2009:35
DOI:
10.1002/ejoc.200901025
Language:
English
Publisher:
Wiley
Publication Date:
2009
detail.hit.zdb_id:
1475010-7