Diastereoselective Synthesis of Pentasubstituted γ??Butyrolactones from Silyl Glyoxylates and Ketones through a Double Reformatsky Reaction

SN Greszler, JS Johnson

文献索引：Greszler, Stephen N.; Johnson, Jeffrey S. Angewandte Chemie, International Edition, 2009 , vol. 48, # 20 p. 3689 - 3691

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被引用次数: 46

摘要

Abstract Three contiguous stereocenters can be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized γ- butyrolactones were assembled rapidly by this approach, in which a ketone is used as the terminal electrophile (see scheme). Secondary transformations of the lactone products enhance their synthetic utility. R 1= Me, H; R 2= alkyl, aryl, CF 3; Bn= benzyl, TBS= tert- ...