92597-09-6Relevant academic research and scientific papers
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.
STEREOCHEMICAL STUDIES-76 SATURATED HETEROCYCLES-63 SYNTHESIS OF CIS- AND TRANS-N-METHYL- AND N-BENZYL-4,5- AND 5,6-TETRAMETHYLENETETRAHYDRO-1,3-OXAZINES; AN X-RAY STUDY OF N-BENZYL-CIS-4,5-TETRAMETHYLENETETRAHYDRO-1,3-OXAZINIUM-PICRATE
Fulop, Ferenc,Bernath, Gabor,Argay, Gyula,Kalman, Alajos,Sohar, Pal
, p. 2053 - 2060 (2007/10/02)
The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-1,3-oxazines (5a,b-8a,b) were synthesized from cis- and trans-N-methyl- and N-benzyl-2-aminomethyl-1-cyclohexanols (1a,b,2 2a,b), and from cis- and trans-N-methy
