Lithium triethylborohydride, LiTEBH, Superhydride
LiBHEt3 is a very strong reducing agent, that is even more efficient than lithium aluminum hydride. LiTEBH for examples enables a fast reduction of carbonyl compounds, esters, acid chlorides, acid anhydrides and tertiary amides to alcohols and disulfides to thiols.
Primary alcohols can be deoxygenated cleanly and in good yields by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in THF at room temperature. Primary alcohols can selectively be reduced in the presence of secondary alcohols. An additional one pot two-step process makes the process simple and convenient.
S. Chowdhury, R. F. Standaert, J. Org. Chem., 2016, 81, 9957-9963.
Reduction of (RS)-N-tert-butanesulfinyl α-halo imines with NaBH4 in THF, in the presence of 10 equiv of MeOH, and subsequent cyclization with KOH afforded the corresponding (RS,S)-N-(tert-butylsulfinyl)aziridines in quantitative yields. On the contrary, its epimer, (RS,R)-N-(tert-butylsulfinyl)aziridine was synthesized in good yields and diastereoselectivity by switchover of the reducing agent from NaBH4 to LiBHEt3.
B. Denolf, E. Leemans, N. De Kimpe, J. Org. Chem., 2007, 72, 3211-3217.