Title of article :
Cross-coupling of nonstabilized aziridinylmagnesiums with alkylhalides catalyzed by Cu(I) iodide: a new synthesis of amines bearing a quaternary chiral center and an asymmetric synthesis of both enantiomers of the amines from one chiral starting material
Author/Authors :
Tsuyoshi Satoh، نويسنده , , Rie Matsue، نويسنده , , Toshinari Fujii، نويسنده , , Satoshi Morikawa، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2001
Pages :
8
From page :
3891
To page :
3898
Abstract :
Treatment of sulfinylaziridines, which were synthesized from 1-chloroalkyl p-tolyl sulfoxides and imines, with ethylmagnesium bromide gave nonstabilized aziridinylmagnesiums by a sulfoxide-magnesium exchange reaction. The cross-coupling of the aziridinylmagnesiums with various kinds of alkylhalides was realized in high yields by using Cu(I) iodide as a catalyst, and the reaction was found to be stereospecific. The coupling products were hydrogenated with Pd(OH)2 in alcohol to give the amines bearing a quaternary chiral center in quantitative yields. Synthesis of both enantiomers of the amines bearing a quaternary chiral center was realized starting from optically active (R)-chloromethyl p-tolyl sulfoxide in good overall yields with perfect asymmetric induction.
Keywords :
asymmetric synthesis of amines , Cross-coupling , aziridinylmagnesium , quaternary chiral center , sulfoxide-magnesium exchange
Journal title :
Tetrahedron
Serial Year :
2001
Journal title :
Tetrahedron
Record number :
1081973
Link To Document :
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