193091-67-7Relevant academic research and scientific papers
Chiral oxime ethers in asymmetric synthesis. Part 5. Asymmetric synthesis of 2-substituted 5- to 8-membered nitrogen heterocycles by oxime addition-ring-closing metathesis
Hunt, James C. A.,Laurent, Pierre,Moody, Christopher J.
, p. 2378 - 2389 (2007/10/03)
Addition of organometallic reagents to chiral oxime ethers 1 derived from an unsaturated aldehyde, or addition of an alkene containing organometallic to chiral aldoxime ethers 2 results in highly stereoselective formation of the hydroxylamines 6. N-Allylation gives the dienes 7 which undergo ring-closing metathesis (RCM) reaction to give the 5-, 6-, and 7-membered nitrogen heterocycles 8. Likewise, the benzyl carbamates 9, also prepared by stereoselective addition to oxime ethers, were converted into dienes 10, which underwent RCM to give the 5- to 8-membered azacycles 11. The oxime addition-RCM protocol is thus a versatile method for the asymmetric synthesis of nitrogen heterocycles, further exemplified by the conversion of the unsaturated heterocycles into chiral piperidines, including the alkaloid (-)-coniine.
Chiral oxime ethers in asymmetric synthesis. 3. Asymmetric synthesis of (R)-N-protected α-amino acids by the addition of organometallic reagents to the ROPHy oxime of cinnamaldehyde
Moody, Christopher J.,Gallagher, Peter T.,Lightfoot, Andrew P.,Slawin, Alexandra M. Z.
, p. 4419 - 4425 (2007/10/03)
A new asymmetric synthesis of α-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N- protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.
Addition of Organolithiums to the (R)-O-(1-Phenylbutyl)hydroxylamine (ROPHy) Oxime of Cinnamaldehyde. Asymmetric Synthesis of α-Aminoacids
Moody, Christopher J.,Lightfoot, Andrew P.,Gallagher, Peter T.
, p. 659 - 660 (2007/10/03)
A new asymmetric synthesis of α-aminoacids is described in which the key step is the diastereoselective addition of organolithium reagents to (R)-O-(1-phenylbutyl) cinnamaldoxime.
