Journal
TETRAHEDRON
Volume 59, Issue 52, Pages 10397-10402Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.06.004
Keywords
reductive coupling; aldimines; ketimines; samarium
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The reductive coupling of aldimines and ketimines by a series of Sm(II)-based reagents (SmI2, SmI2-HMPA, SmBr2, Sm{N[Si(CH3)(3)](2)}(2), and SmI2/triethylamine/water) were examined. In general, aldimines and ketimines were efficiently reduced or coupled using reductants that are more powerful than SmI2, and the use of Sm{N[Si(CH3)(3)](2)}(2) led to higher diastereoselectivities in reductive coupling reactions. Surprisingly, only the combination of SMI2/triethylamine/water was capable of reducing and coupling para-substituted benzaldimines and coupling ketimines. (C) 2003 Elsevier Ltd. All rights reserved.
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