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- W2121483586 abstract "1,3-Oxazinan-6-ones were used to generate substituted β 2,2,3 -substituted amino acid derivatives. The enolates of 1,3-oxazinan-6-ones were trans-selectively intercepted with electrophiles. This alkylation was subsequently optimized for a one-pot dialkylation to form 5,5-disubstituted oxazinanones. The initial 5-monomethylated compounds could be enolized and then diastereoselectively intercepted with different electrophiles to form differentially 5,5-disubstituted products. The 5,5-dialkylated oxazinanones were then transformed to N -methyl β 2,2,3 -substituted amino acids by reductive cleavage. Hydrolysis or solvolysis of the oxazinanones afforded β 2,2,3 -substituted amino acids or esters, respectively. The chemistry thus provides access to a range of symmetrical and stereopure β 2,2,3 -substituted amino acids and further establishes 1,3-oxazinan-6-ones as useful intermediates." @default.
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- W2121483586 date "2012-06-01" @default.
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- W2121483586 title "Diastereoselective synthesis of highly functionalized β2,2,3-substituted amino acids from 4-substituted-1,3-oxazinan-6-ones" @default.
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- W2121483586 doi "https://doi.org/10.1016/j.tet.2012.04.012" @default.
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