281192-53-8Relevant academic research and scientific papers
Diastereoselective LiAlH4 reduction of chiral ketone hydrazones derived from (R)-(-)-2-aminobutan-1-ol
Bataille, Patricia,Paterne, Michel,Brown, Eric
, p. 1165 - 1181 (2000)
Various chiral N,N-dialkylhydrazines were prepared in four to five steps from (R)-(-)-2-aminobutan-1-ol 6. They reacted with various prochiral ketones, thus giving the corresponding hydrazones. Reduction of the latter by means of LiAlH4 afforded N,N,N'-trisubstituted hydrazines whose d.e.s were in the range 43-100%. Interestingly, LiAlH4 reduction of the four N-trifluoroethylhydrazones 34 and 38-40 yielded the hydrazines 46 and 48-50, respectively, and with d.e.s=100% by 1H and 13C NMR. Copyright (C) 2000 Elsevier Science Ltd.
