15148-17-1Relevant articles and documents
Parallel synthesis using Mannich-type three-component reactions and 'field synthesis' for the construction of an amino alcohol library
Kobayashi, Shu,Moriwaki, Mitsuhiro,Akiyama, Ryo,Suzuki, Shu,Hachiya, Iwao
, p. 7783 - 7786 (1996)
An amino alcohol library was constructed by parallel synthesis based on Mannich-type three-component reactions of aldehydes, amines, and polymer-supported silyl enol ethers, followed by reductive cleavage from the supports. 'Field Synthesis', which provid
Gold-Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Catalytic Reaction Pathways to Access 1,3-Amino Alcohols, 3-Hydroxyketones, or 3-Aminoketones
Laserna, Victor,Porter, Michael J.,Sheppard, Tom D.
, p. 11391 - 11406 (2019/09/30)
A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. First, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxyimines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-amino alcohols with high syn selectivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway. The utility of the new chemistry was exemplified by the one-pot synthesis of a selection of N-arylpyrrolidines and N-arylpiperidines. A mechanism for the hydroamination has been proposed on the basis of experimental studies and density functional theory calculations.
Chemo- and diastereoselective reduction of β-enamino esters: A convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters
Bartoli,Cimarelli,Marcantoni,Palmieri,Petrini
, p. 5328 - 5335 (2007/10/02)
Convenient procedures for the chemo- and diastereoselective reduction of b-enamino esters 1 are described. Both cis- and trans-γ-amino alcohols 2 or b-amino esters 3 can be prepared by reduction of b-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Na/i-PrOH or NaHB(OAc)3/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric γ-amino alcohols 2 and β-amino esters 3 obtained are established by 1H and 13C NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.