3-Aminopyrrolidines via ring rearrangement of 2-aminomethylazetidines. Synthesis of(-)-absouline

被引:56
作者
Vargas-Sanchez, M [1 ]
Couty, F [1 ]
Evano, G [1 ]
Prim, D [1 ]
Marrot, J [1 ]
机构
[1] Univ Versailles St Quentin Yvelines, CNRS, UMR 8086, Lab SIRCOB, F-78035 Versailles, France
关键词
D O I
10.1021/ol052388e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.
引用
收藏
页码:5861 / 5864
页数:4
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