trans-Hydroxypipecolic acids of both L- and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively, starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids
Total synthesis of both enantiomers of trans- Beta-hydroxypipecolic acid
1997
Abstract
trans-Hydroxypipecolic acids of both L- and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively, starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acidsFile in questo prodotto:
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