Ruiting Liu, Jingqian Wei, Bangguo Wei
Dec 1, 2008
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Tetrahedron-asymmetry
Abstract
Abstract An efficient asymmetric synthesis of the 2-hydroxymethyl 3,6-disubstituted piperidine alkaloid, (−)-deoxoprosophylline, is described. The key step of this route is the SmI 2 -mediated cross-coupling of chiral N-tert -butanesulfinyl imine 9 with aldehyde 11 to construct hydroxymethyl-β-amino alcohol 12b in 83% yield and high diastereoselectivity (>99%, de).