Kinetic resolution and parallel kinetic resolution of methyl (±)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives
| dc.contributor.author | Davies, Stephen G. | |
| dc.contributor.author | Garner, A. Christopher | |
| dc.contributor.author | Long, Marcus J. C. | |
| dc.contributor.author | Morrison, Rachel M. | |
| dc.contributor.author | Roberts, Paul M. | |
| dc.contributor.author | Savory, Edward D. | |
| dc.contributor.author | Smith, Andrew D. | |
| dc.contributor.author | Sweet, Miles J. | |
| dc.contributor.author | Withey, Jonathan M. | |
| dc.date.accessioned | 2016-01-12 | |
| dc.date.accessioned | 2022-05-27T01:13:48Z | |
| dc.date.available | 2022-05-27T01:13:48Z | |
| dc.date.issued | 2005 | |
| dc.description.abstract | Conjugate addition of lithium dibenzylamide to methyl 5-isopropyl, 5-phenyl- and 5-tert-butyl-cyclopentene-1-carboxylates occurs with high levels of substrate control (>88% de), with preferential addition to the face of the cyclic α,β-unsaturated acceptor anti- to the stereodirecting 5-alkyl substituent. Treatment of a range of methyl (±)-5-alkyl-cyclopentene-1-carboxylates with both lithium (±)-N-benzyl-N-α-methylbenzylamide and lithium (±)-N-3,4-dimethoxybenzyl-N-α-methylbenzylamide indicates significant enantiorecognition in their mutual kinetic resolutions, with preferential addition anti- to the 5-alkyl substituent, giving the 1,2-syn-1,5-anti-arrangement (E >16) after enolate protonation anti- to the amino functionality. The kinetic resolution of a range of methyl (±)-5-alkyl-cyclopentene-1-carboxylates with lithium (S)-N-benzyl-N-α-methylbenzylamide, and their efficient parallel kinetic resolution with a pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-α-methylbenzylamide and lithium (R)-N-3,4-dimethoxybenzyl-N-α-methylbenzylamide are also demonstrated, giving a range of 5-alkyl-cispentacin derivatives in >98% de and high ee after N-deprotection. | |
| dc.description.uri | http://library.macewan.ca/cgi-bin/SFX/url.pl/7M6 | |
| dc.identifier.citation | Davies, S. G., Garner, A. C., Long, M. J., Morrison, R. M., Roberts, P. M., Savory, E. D., ... & Withey, J. M. (2005). Kinetic resolution and parallel kinetic resolution of methyl (±)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives. Organic & Biomolecular Chemistry, 3(15), 2762-2775. doi: 10.1039/B506339F | |
| dc.identifier.doi | https://doi.org/ 10.1039/B506339F | |
| dc.identifier.uri | https://hdl.handle.net/20.500.14078/280 | |
| dc.language | English | |
| dc.language.iso | en | |
| dc.rights | All Rights Reserved | |
| dc.subject | kinetic resolution | |
| dc.subject | parallel kinetic resolution | |
| dc.title | Kinetic resolution and parallel kinetic resolution of methyl (±)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives | en |
| dc.type | Article | |
| dspace.entity.type |