Asymmetric synthesis of tetrahydrolipstatin and valilactone

SC Case-Green, SG Davies, PM Roberts…

Index: Case-Green, Stephen C.; Davies, Stephen G.; Roberts, Paul M.; Russell, Angela J.; Thomson, James E. Tetrahedron Asymmetry, 2008 , vol. 19, # 22 p. 2620 - 2631

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Citation Number: 26

Abstract

The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5) Fe (CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation–cyclisation process gives access to β-substituted and α, β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and ...