Parallel kinetic resolution of tert-butyl (RS)-3-alkyl–cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl–cispentacin derivatives - MacEwan Users Only

Davies, S. G., Garner, A. C., Long, M. J. C., Smith, A. D., Sweet, M. J., & Withey, J. (2004). Parallel kinetic resolution of tert-butyl (RS)-3-alkyl–cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl–cispentacin derivatives.
Metadata
TitleParallel kinetic resolution of tert-butyl (RS)-3-alkyl–cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl–cispentacin derivatives
Author(s)Davies, Stephen G.; Garner, A. Christopher; Long, Marcus J. C.; Smith, Andrew D.; Sweet, Miles J.; Withey, Jonathan
Date2004
Keyword(s)beta-amino acids, catalysts, esters
DescriptionThe double mutual kinetic resolution of tert-butyl (RS)-3-benzyl-cyclopentene-1-carboxylate with a 50 : 50 mixture of lithium (RS)-N-benzyl-N-alpha-methylbenzylamide and lithium (RS)-N-3,4-dimethoxybenzyl-N-alpha-methylbenzylamide gives, after protonation with 2,6-di-tert-butylphenol, a 50 : 50 mixture of the readily separable N-benzyl-(1SR,2RS,3RS,alphaRS)- and N-3,4-dimethoxybenzyl-(1SR,2RS,3RS,alphaRS)-beta-amino esters in >98% de in each case. This product distribution indicates that these amides react at very similar rates and with no mutual interference to furnish readily separable products, and are thus ideal for parallel kinetic resolution. The efficient parallel kinetic resolution ( E > 65) of a range of tert-butyl (RS)-3-alkyl-cyclopentene-1-carboxylates with a pseudoenantiomeric mixture of homochiral lithium (S)-N-benzyl-N-alpha-methylbenzylamide and lithium (R)-N-3,4-dimethoxybenzyl-N-alpha-methylbenzylamide gives, after separation and N-deprotection, a range of carboxylate protected 3-alkyl-cispentacin derivatives in >98% de and >95% ee.
Peer ReviewedYes
Type of ItemJournal Articles
DOIdoi:10.1039/B407560A
Publication InformationDavies, S., Garner, A., Long, M., Smith, A., Sweet, M., & Withey, J. (2004). Parallel kinetic resolution of tert-butyl (RS)-3-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl-cispentacin derivatives. Organic & Biomolecular Chemistry, 2(22), 3355-3362. doi:10.1039/B407560A
MacEwan Users Onlyhttp://library.macewan.ca/cgi-bin/SFX/url.pl/7M8
LanguageEnglish
RightsAll Rights Reserved