127001-22-3Relevant academic research and scientific papers
(1S)-(Z)-2-benzyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide
Drouard,Py,Averbuch,Philouze,Vallee
, p. 1079 - 1080 (2001)
The preparation and crystal structure of (1S)-(Z)-2-benyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide was described. A dihedral angle of 11.16 (2)° was observed between the C5/N1/C6 and N1/C6/H11 planes. There were three bonds originating from the N atom, to an oxygen atom, to a Csp2 and to a Csp3 atom. The nitrogen atom substituent of the nitrone function adopted a conformation which minimizes the 1,3-allylic strain.
Diastereoselective addition of terminal alkynes to chiral nitrones: Asymmetric synthesis of propargylic N-hydroxylamines
Patel, Samir K.,Py, Sandrine,Pandya, Shashi U.,Chavant, Pierre Y.,Vallee, Yannick
, p. 525 - 528 (2007/10/03)
1,3-Asymmetric induction in the Et2Zn-catalyzed addition of terminal alkynes was studied with nitrones bearing a chiral auxiliary on their nitrogen atom. The obtained propargylic N-hydroxylamines were generally isolated in good yields and with satisfactory to excellent diastereoselectivities.
Synthesis of chiral, nonracemic methyleneaziridines derived from β-amino alcohols
Ince, Julie,Ross, Tracey M.,Shipman, Michael,Ennis, David S.
, p. 3397 - 3406 (2007/10/03)
An efficient three step process for the synthesis of chiral, nonracemic methyleneaziridines derived from homochiral β-amino alcohols is described. Methyleneaziridines 4a-e produced using this chemistry have been shown to possess high enantiomeric purities
Enantioselective Synthesis of Primary Amines via Grignard Additions to Stereogenic N-(α-Phenyl-β-(benzyloxy)ethyl)nitrones
Chang, Zen-Yu,Coates, Robert M.
, p. 3475 - 3483 (2007/10/02)
Addition of a wide range of Grignard to C-aryl- and C-alkyl-N-(α-phenyl-β-(benzyloxy)ethyl)nitrones (4-7) occurred with high diastereoselectivity (90:10 to 97:3 ratios) and good yields (56 - 97percent).Notable exceptions are allyl- and (o-methoxyphenyl)magnesium bromides (low selectivity but satisfactory yields) and isopropyl- and tert-butylmagnesium chlorides (high selectivity but 33 - 34percent yields) with C-phenylnitrone 4.The relative stereochemistry of hydroxylamine adducts 8a,b (from reaction of 4 with CH3MgBr) and 19a,b (from C-pentylnitrone 7 with MeMgBr) was provenby various correlations and/or by degradation to enantiomerically enriched amines.The other stereochemical assignments are based upon 1H NMR spectral and polarity correlations and/or by analogy to the two proven cases.The configuration of the major product can be rationalized by assuming that the Grignard reagents attack the nitrone face opposite to the pseudoequatorial N-(α-phenyl) group in a six-membered magnesium chelate (27 -> 28). 1H NMR spectral evidence indicates that a 1:1 complex of nitrone 4 and magnesium bromide exists in a chelated structure (29B) in CD2Cl2.Enantioselective syntheses of (S)-α-phenylethylamine (94percent ee) and (S)-2-heptylamine (82percent ee) were accomplished in five steps (33-39percent overall yields) from optically pure (S)-nitrones 4 and 7.
