4641-52-5Relevant articles and documents
Boranes in Synthesis. 6. A New Synthesis of β-Amino Alcohols from Epoxides. Use of Lithium Amides and Aminoborane Catalysts To Synthesize β-Amino Alcohols from Terminal and Internal Epoxides in High Yield
Harris, Clifford E.,Fisher, Gary B.,Beardsley, David,Lee, Lawrence,Goralski, Christian T.,et al.
, p. 7746 - 7751 (1994)
A study of the conversion of terminal and internal epoxides to the corresponding β-amino alcohols using simple primary and secondary lithium amides has been carried out.Thus, styrene oxide and 1,2-epoxydodecane react directly with primary and secondary lithium amides in THF at 25 deg C to give a single regioisomer of the corresponding β-amino alcohols in 80-100percent isolated yields.Since internal epoxides are known to yield predominantly allylic alcohols when reacted with lithium amides, we employed a series of aminoborane Lewis-acid catalists, generated in situ, to suppress formation of the allylic alcohols.Thus, the reaction of cyclohexene oxide with a variety of primary and secondary lithium amides at 34 deg C in diethyl ether in the presence of a catalytic amount of B-bromo-9-BBN afforded the corresponding β-amino alcohols in 70-95percent isolated yield.
Dehydrogenation of cyclic tertiary amines with neighbouring of enantiomeric nucleophiles
M?hrle, Hans,Berkenkemper, Thomas
, p. 435 - 443 (2007/10/03)
For stereochemical investigation of their dehydrogenation, the enantiomers of the aminoalcohols 1, 2, and 3 were prepared from optically active sources, while the enantiomers of the diamines 8 and 9 were available by resolution of the racemates. The pure antipodes of 1, 2, and 3 reacted with mercury(II)-EDTA by a twofold dehydrogenation via intermediate participation of the neighbouring alcoholic group to the optically active lactams 5, 6, and 7 under complete retention of configuration. In the same manner the diamines 8 and 9 generated by four electron withdrawal the cycloamidines 10 and 11.
