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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 valilactone. © 2008 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2008.11.012

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

17/11/2008

Volume

19

Pages

2620 - 2631