通过酰基克莱森反应和碘内酯化路线实现反式-3,4-二烷基-γ-丁内酯的不对称合成。
Asymmetric synthesis of trans-3,4-dialkyl-gamma-butyrolactones via an acyl-Claisen and iodolactonization route.
作者信息
Xu Qun, Rozners Eriks
机构信息
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
出版信息
Org Lett. 2005 Jul 7;7(14):2821-4. doi: 10.1021/ol050578j.
[reaction: see text] A new, efficient, and general asymmetric synthesis of enantiomerically pure trans-3,4-dialkyl-gamma-lactones has been developed. The key steps are (1) copper-catalyzed three-component coupling of chiral amine, aldehyde, and alkyne, (2) acyl-Claisen rearrangement, and (3) iodolactonization. The products, chiral gamma-lactones, are versatile synthetic intermediates and structural units of natural products and modified nucleosides.
[反应：见正文] 已开发出一种对映体纯的反式-3,4-二烷基-γ-内酯的新型、高效且通用的不对称合成方法。关键步骤包括：(1) 铜催化的手性胺、醛和炔烃的三组分偶联；(2) 酰基-克莱森重排；(3) 碘内酯化。产物手性γ-内酯是通用的合成中间体以及天然产物和修饰核苷的结构单元。
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