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

Author
Davies, Stephen G.
Garner, A. Christopher
Long, Marcus J. C.
Smith, Andrew D.
Sweet, Miles J.
Withey, Jonathan
Faculty Advisor
Date
2004
Keywords
beta-amino acids , catalysts , esters
Abstract (summary)
The 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.
Publication Information
Davies, 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
DOI
Notes
Item Type
Article
Language
English
Rights
All Rights Reserved