112712-55-7Relevant 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.
A practical method for the acylation of 2-imidazolidinone and 2-oxazolidinone chiral auxiliaries with 2-bromoacyl halides
Candeias,Jenkins,Ribeiro,Afonso,Caddick
, p. 3241 - 3254 (2007/10/03)
Optimised conditions for the acylation of (S)-4-(1-methyl-ethyl)-oxazolidin-2-one 4, (R)-4-phenyloxazolidin-2-one 5 and 4-(R), (5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 3 with 2-bromoacyl halides were developed. For imidazolidin-2-one 3 the optimum con
Ephedrine-Derived Imidazolidin-2-ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis
Drewes, Siegfried E.,Malissar, Dean G. S.,Roos, Gregory H. P.
, p. 2663 - 2674 (2007/10/02)
The scope of the readily available (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one (4) and its 4-cyclohexyl analogue 6 as practical, efficient chiral auxiliaries has been demonstrated.The enolate chemistry of their N-acyl derivatives exhibits features which recommend their use in asymmetric synthesis.The stereoselective boron-mediated aldol as well as alkylation and acylation results are presented.The steric control benefit derived by conversion of phenyl to cyclohexyl is highlighted. - Key Words: Imidazolidin-2-one, (4R,5S)-1,5-dimethyl-5-phenyl- or cyclohexyl- / (-)-Ephedrine / Stereoselective aldol / alkylation, acylation
A new approach to 2-phenylthioalcohols in high optical purity
Orena,Porzi,Sandri
, p. 3797 - 3800 (2007/10/02)
2-Phenylthioalcohols are prepared in high optical purity by alkylation of chiral imides of 2-phenylthioacetic acid, obtained starting from chiral imidazolidin-2-ones.
