140451-61-2Relevant articles and documents
Stereoselective synthesis of quaternary center bearing azetines and their β-amino acid derivatives
MacNevin, Christopher J.,Moore, Rhonda L.,Liotta, Dennis C.
, p. 1264 - 1269 (2008)
(Chemical Equation Presented) We describe here the use of a stable, four-membered azetine heterocycle for the preparation of highly substituted β-amino acid derivatives. Imidazolidinone chiral auxiliaries were found to eliminate a competitive reaction pathway that had been present under previously reported conditions for azetine synthesis. The ephedrine derived imidazolidin-2-one 21 was allowed to react as its chlorotitanium enolate with O-methyl or -benzyl oximes under optimized conditions to gain improved access to azetines at the gram scale. The azetines were further found to undergo alkylation with complete diastereocontrol, affording the creation of a quaternary center. Subsequent ring opening with benzoyl chloride and auxiliary cleavage provided the corresponding β2,2,3-amino carbonyl derivatives in good yields.
ADDITION OF ARYLLITHIUM COMPOUNDS TO OXIME ETHERS
Rodriques, Karen E.,Basha, Anwer,Summers, James B.,Brooks, Dee W.
, p. 3455 - 3458 (2007/10/02)
Addition of non-stabilized organolithium reagents to O-alkyl aldoximes in the presence of boron trifluoride etherate gives rise to O-alkyl hydroxylamines.The Z oxime isomer preferentially reacts under these reaction conditions.
