240433-16-3Relevant academic research and scientific papers
Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes
Hunt, James C. A.,Lloyd, Cephas,Moody, Christopher J.,Slawin, Alexandra M. Z.,Takle, Andrew K.
, p. 3443 - 3454 (2007/10/03)
Addition of organolithium or Grignard reagents to (R)- or (S)-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride-diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N-O bond with zinc-acetic acid-ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77-100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-aminb alcohols 5. The Royal Society of Chemistry 1999.
Addition of 2-lithiothiazoles to ROPHy/SOPHy aldoximes: Asymmetric synthesis of 1-(2-thiazolyl)ethylamines
Moody, Christopher J.,Hunt, James C. A.
, p. 984 - 986 (2007/10/03)
A new asymmetric synthesis of 1-(2-thiazolyl)ethylamines is described in which the key step is the diastereoselective addition of 2-lithiothiazoles to O-(1-phenylbutyl) aidoximes.
