Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-1-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate

Stephen G. Davies; David Díez; Mohamed M. El Hammouni; A. Christopher Garner; Narciso M. Garrido; Marcus J. C. Long; Rachel M. Morrison; Andrew D. Smith; Miles J. Sweet; Jonathan M. Withey

doi:10.1039/B308855C

Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-1-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate

Stephen G. Davies,*^a David Díez,^b Mohamed M. El Hammouni,^b A. Christopher Garner,^a Narciso M. Garrido,^b Marcus J. C. Long,^a Rachel M. Morrison,^a Andrew D. Smith,^a Miles J. Sweet^a and Jonathan M. Withey^a

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^a The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK
E-mail: steve.davies@chemistry.oxford.ac.uk

^b Departmento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain

Abstract

Comparison of the kinetic and parallel kinetic resolutions of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate allows for the efficient synthesis of both (1R,2S,5S)- and (1S,2R,5R)-enantiomers of methyl 2-amino-5-tert-butyl-cyclopentane-1-carboxylate.

Chemical Communications

Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-1-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate

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Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-1-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate

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