Palladium[O]-mediated aminospirocyclization of tertiary allylic sulfones. Stereospecific construction of the azabicyclic ring system of cephalotaxine.

被引:16
作者
Jin, ZD [1 ]
Fuchs, PL [1 ]
机构
[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907
关键词
D O I
10.1016/0040-4039(96)01112-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tertiary allylic sulfones which bear a secondary aminopropyl moiety undergo smooth palladium [0]-mediated spirocyclization. The reaction proceeds via a pi-allyl intermediate and the resultant azabicyclic product is formed with net retention of sulfone stereochemistry. The use of tetramethylguanidine as companion base is required For high yielding reactions. Copyright (C) 1996 Elsevier Science Ltd
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页码:5253 / 5256
页数:4
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