4641-52-5Relevant academic research and scientific papers
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.
Borrowing hydrogen methodology for amine synthesis under solvent-free microwave conditions
Watson, Andrew J. A.,Maxwell, Aoife C.,Williams, Jonathan M. J.
supporting information; experimental part, p. 2328 - 2331 (2011/05/17)
Application of microwave heating to the Borrowing Hydrogen strategy to form C-N bonds from alcohols and amines is presented, removing the need for solvent and reducing the reaction times while still yielding results comparable with those using thermal heating.
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.
Neighbour Group Participation with Reductions and Hydride Abstractions
Moehre, H.,Kamper, Ch.
, p. 512 - 520 (2007/10/02)
The reduction of N-(2-hydroxyalkyl)lactams with diisobutylaluminium hydride and the hydride ion abstraction of the corresponding amino alcohols give under neighbour group participation the fused oxazolidines.
