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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. ...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
19
Issue:
24
Pages:
2870-2881
Publication date:
2008-12-12
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:4bb02c8a-c64b-4553-8e37-4e1c8dcdb943
Source identifiers:
41107
Local pid:
pubs:41107
Language:
English

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