Tetrahedron

Reduction and reductive coupling of imines by Sm (II)-based reagents

…, BW Knettle, A Dahlén, G Hilmersson, RA Flowers

Index: Kim, Myeongseob; Knettle, Brian W.; Dahlen, Anders; Hilmersson, Goeran; Flowers II, Robert A. Tetrahedron, 2003 , vol. 59, # 52 p. 10397 - 10402

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Citation Number: 56

Abstract

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 ...