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Synfacts 2010(1): 0068-0068  
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

Contributor(s): Mark Lautens, Jane Panteleev
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
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Publication History

Publication Date:
21 December 2009 (online)

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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.