Kinetic resolution of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates for the synthesis of homochiral 3-alkyl-cispentacin and 3-alkyl-transpentacin derivatives.

Journal article

High levels of stereocontrol are observed in the conjugate addition of lithium dibenzylamide to tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates (alkyl = Et, Bn), with addition occurring exclusively anti- to the 3-alkyl substituent. Treatment of a range of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates (alkyl = Et, Bn, (i)Pr, (t)Bu) with lithium (RS)-N-benzyl-N-[small alpha]-methylbenzylamide indicates that good enantiorecognition is observed (E > 80) in their mutual kinetic resoluti...

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Authors: Bunnage, M; Davies, S; Parkin, R; Roberts, P; Smith, A

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 2
• Issue: 22
• Pages: 3337-3354
• Publication date: 2004-11-01
• DOI: 10.1039/b407559e
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Carboxylic Acids; Kinetics; Lithium Compounds; Cycloleucine; Chemistry, Organic; Amides; Pentetic Acid; Stereoisomerism; Molecular Mimicry