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• W2013571488 abstract "A new type of parallel kinetic resolution (PKR) is reported in which quasienantiomers with very similar reactivities give products whose chromatographic properties diverge upon the addition of fluoride. This concept of a reactivity/affinity switch is applied to the PKR of cyclopropene carboxylic acids with all-carbon quaternary centers. This is the first application of α-amino acid quasienantiomers in PKR, and it is a complementary approach for acyltransfer systems where the asymmetry is induced by the nucleophile rather than the leaving group. Excellent diastereoselectivities (ranging from 90:10 to 99.5:5) and good yields were obtained for both quasienantiomeric products, and the reactions can be run on significant scale because the separation is trivial. High-level DFT calculations (B3LYP functional with the 6-31+G(d,p) basis set) provided transition-state structures with relative energies that are in accord with the experimental observations." @default.
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• W2013571488 date "2004-03-20" @default.
• W2013571488 modified "2023-09-22" @default.
• W2013571488 title "A Reactivity/Affinity Switch for Parallel Kinetic Resolution: α-Amino Acid Quasienantiomers and the Resolution of Cyclopropene Carboxylic Acids" @default.
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• W2013571488 doi "https://doi.org/10.1021/ja049779t" @default.
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