870654-46-9Relevant academic research and scientific papers
Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 158 - 160 (2011/03/20)
Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.
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.
