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- W2069436891 abstract "A new and efficient method is presented for the preparation of the N-Boc-protected cyclopropane analogue of valine, 1-(N-tert-butoxycarbonyl)amino-2,2-dimethylcyclopropanecarboxylic acid, both in racemic and enantiomerically pure forms. Cyclopropanation of the exocyclic double bond of 2-phenyl-4-isopropylidene-5(4H)-oxazolone with diazomethane followed by elaboration of the heterocyclic moiety provided multigram quantities of the racemic target compound. Subsequent HPLC resolution of a racemic precursor on a noncommercial chiral stationary phase has given access to enantiomerically pure products. Almost 1.5 g of the first-eluted enantiomer and 1.0 g of the second-eluted enantiomer have been isolated in optically pure form using a 150 × 20 mm ID column containing mixed 10-undecenoate/3,5-dimethylphenylcarbamate of cellulose covalently bonded to allylsilica gel with a mixture of hexanes/tert-butyl methyl ether/ethyl acetate as the mobile phase. Chirality 17:22–29, 2005. ©2004 Wiley-Liss, Inc." @default.
- W2069436891 created "2016-06-24" @default.
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- W2069436891 date "2004-10-28" @default.
- W2069436891 modified "2023-10-03" @default.
- W2069436891 title "Synthesis and HPLC enantioseparation of the cyclopropane analogue of valine (<scp>c</scp><sub>3</sub>Val)" @default.
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- W2069436891 doi "https://doi.org/10.1002/chir.20091" @default.
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