1007358-38-4Relevant academic research and scientific papers
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 (2008/04/05)
(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.
