Tetrahedron: Asymmetry

SmI 2-coupling reaction of chiral non-racemic α-bromo-α′-sulfinyl ketones with imines: synthesis of enantiomerically pure 2-methyl-3-amino-1-ol moieties

M Barbarotto, J Geist, S Choppin, F Colobert

文献索引：Barbarotto, Marie; Geist, Julie; Choppin, Sabine; Colobert, Francoise Tetrahedron Asymmetry, 2009 , vol. 20, # 24 p. 2780 - 2787

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被引用次数: 11

摘要

Chiral non-racemic α-bromo-α′-sulfinyl ketones were shown to react with imines in the presence of SmI2 to give the corresponding 1, 3-aminoketo derivatives with good syn- diastereoselectivity. Further reduction of these adducts either with DIBAL-H only or with DIBAL-H in the presence of Yb (OTf) 3 afforded syn-and anti-2-methyl-3-amino-1-ol moieties, respectively, in good yields and diastereoselectivities.