Journal article

Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Abstract:: Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl-N-(α-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. © 2008 Elsevier Ltd. All rights reserved.

Publication status:: Published

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APA Style

Davies, S., Durbin, M., Hartman, S., Matsuno, A., Roberts, P., Russell, A., Smith, A., Thomson, J., & Toms, S. (2008). Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives. TETRAHEDRON-ASYMMETRY, 19(24), 2870–2881.

MLA Style

Davies, S, et al. “Parallel Kinetic Resolution of Tert-Butyl (RS)-6-Alkyl-Cyclohex-1-Ene-Carboxylates for the Asymmetric Synthesis of 6-Alkyl-Substituted Cishexacin Derivatives.” TETRAHEDRON-ASYMMETRY, vol. 19, no. 24, 2008, pp. 2870–81.

Chicago Style

Davies, S, M Durbin, S Hartman, et al. 2008. “Parallel Kinetic Resolution of Tert-Butyl (RS)-6-Alkyl-Cyclohex-1-Ene-Carboxylates for the Asymmetric Synthesis of 6-Alkyl-Substituted Cishexacin Derivatives.” TETRAHEDRON-ASYMMETRY 19 (24): 2870–81.
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Publisher copy:: 10.1016/j.tetasy.2008.11.019

Authors

+ Davies, S More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Durbin, M More by this author

Role:: Author

+ Hartman, S More by this author

Role:: Author

+ Matsuno, A More by this author

Role:: Author

+ Roberts, P More by this author

Role:: Author

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Journal:: TETRAHEDRON-ASYMMETRY More from this journal
Volume:: 19
Issue:: 24
Pages:: 2870-2881
Publication date:: 2008-12-12
DOI:: 10.1016/j.tetasy.2008.11.019
EISSN:: 1362-511X
ISSN:: 0957-4166

Language:: English
Pubs id:: pubs:41107
UUID:: uuid:4bb02c8a-c64b-4553-8e37-4e1c8dcdb943
Local pid:: pubs:41107
Source identifiers:: 41107
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_4bb02c8ac64b45538e374e1c8dcdb943

Terms of use

Copyright date:: 2008

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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