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Issue 22, 2004
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Parallel kinetic resolution of tert-butyl (RS)-3-alkyl–cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl–cispentacin derivatives

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Abstract

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-α-methylbenzylamide and lithium (RS)-N-3,4-dimethoxybenzyl-N-α-methylbenzylamide gives, after protonation with 2,6-di-tert-butylphenol, a 50 : 50 mixture of the readily separable N-benzyl-(1SR,2RS,3RSRS)- and N-3,4-dimethoxybenzyl-(1SR,2RS,3RSRS)-β-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-α-methylbenzylamide and lithium (R)-N-3,4-dimethoxybenzyl-N-α-methylbenzylamide gives, after separation and N-deprotection, a range of carboxylate protected 3-alkyl–cispentacin derivatives in >98% de and >95% ee.

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

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Publication details

The article was received on 20 May 2004, accepted on 17 Aug 2004 and first published on 20 Oct 2004


Article type: Paper
DOI: 10.1039/B407560A
Citation: Org. Biomol. Chem., 2004,2, 3355-3362
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    Parallel kinetic resolution of tert-butyl (RS)-3-alkyl–cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl–cispentacin derivatives

    S. G. Davies, A. C. Garner, M. J. C. Long, A. D. Smith, M. J. Sweet and J. M. Withey, Org. Biomol. Chem., 2004, 2, 3355
    DOI: 10.1039/B407560A

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