The synthesis of (2S,4R)- and (2R,4R)-4-hydroxypipecolic acid has been realized from commercial ethyl (R)-4-cyano-3-hydroxybutanoate through palladium-catalyzed methoxycarbonylation of a 4-hydroxy-substituted lactam-derived vinyl phosphate followed by the stereocontrolled reduction of the enamine double bond. The stereoselective hydrogenation of the suitably 4-hydroxy-protected enantiomer afforded the cis-(2S,4R)-4-hydroxypipecolic acid product, obtained in 66% overall yield over seven steps. The trans-product (42% overall yield over 8 steps) was instead obtained by hydride conjugate addition to the same alpha,beta-unsaturated ester.

A short and convenient synthesis of enantiopure cis- and trans-4-hydroxypipecolic acid / E.G.Occhiato; D.Scarpi; A.Guarna; S.Tabasso; A.Deagostino; C.Prandi. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - ...:(2009), pp. 3611-3616. [10.1055/s-0029-1216979]

A short and convenient synthesis of enantiopure cis- and trans-4-hydroxypipecolic acid

OCCHIATO, ERNESTO GIOVANNI;SCARPI, DINA;GUARNA, ANTONIO;
2009

Abstract

The synthesis of (2S,4R)- and (2R,4R)-4-hydroxypipecolic acid has been realized from commercial ethyl (R)-4-cyano-3-hydroxybutanoate through palladium-catalyzed methoxycarbonylation of a 4-hydroxy-substituted lactam-derived vinyl phosphate followed by the stereocontrolled reduction of the enamine double bond. The stereoselective hydrogenation of the suitably 4-hydroxy-protected enantiomer afforded the cis-(2S,4R)-4-hydroxypipecolic acid product, obtained in 66% overall yield over seven steps. The trans-product (42% overall yield over 8 steps) was instead obtained by hydride conjugate addition to the same alpha,beta-unsaturated ester.
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3611
3616
E.G.Occhiato; D.Scarpi; A.Guarna; S.Tabasso; A.Deagostino; C.Prandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/366488
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