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Synfacts 2010(1): 0068-0068
DOI: 10.1055/s-0029-1218482
DOI: 10.1055/s-0029-1218482
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Reduction of Lactones with Samarium Iodide
D. Parmar, L. A. Duffy, D. V. Sadasivam, H. Matsubara, P. A. Bradley, R. A. Flowers II, D. J. Procter*
University of Manchester, Pfizer Global R&D, Sandwich, UK; Lehigh University, Bethlehem, USA; Osaka Prefecture University, Japan
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Significance
Following a preliminary report (J. Am. Chem. Soc. 2008, 130, 1136) more detailed mechanistic investigations on the reduction of six-membered cyclic lactones through samarium(II) are described. Additionally, an intermediate in the reduction is trapped with an intramolecular alkene acceptor giving bicyclic ketones in high diastereoselectivity. Previous reductions of esters under Sm(II) are limited to aromatic substrates.