139255-94-0

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 67-64-1 acetone 

Downstream Products

• 143669-02-7 2-Bromo-1-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-butan-1-one 
• 143668-72-8 fumaric bis<2,2-dimethyl-5(R)-phenyl-1,3-oxazolidinide> 
• 143668-73-9 ethenetricarboxylic acid, 1,1-dimethyl ester, 2-<2,2-dimethyl-5(R)-phenyl-1,3-oxazolidinide> 
• 159463-49-7 (4R)-2,2-dimethyl-4-phenyl-3-[(E)-3-phenylpropenoyl]oxazolidine 
• 139255-99-5 N-<(1R)-2-hydroxy-1-phenylethyl>-(5R)-3-phenyl-2-isoxazoline-5-carboxamide 
• 139256-00-1 N-<(1R)-2-hydroxy-1-phenylethyl>-(5S)-3-phenyl-2-isoxazoline-5-carboxamide 
• 136570-14-4 (S)-3-Cyclohexyl-1-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-2-(pyridin-2-ylsulfanyl)-propan-1-one 
• 136570-16-6 (R)-3-Cyclohexyl-1-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-2-(pyridin-2-ylsulfanyl)-propan-1-one 
• 143668-79-5 2-iodobutyric 2',2'-dimethyl-5'(R)-phenyl-1',3'-oxazolidinide 
• 136570-26-8 2-[1-Cyclohexyl-2-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-malonic acid dimethyl ester 
• 143669-05-0 2-Cyclohexyl-1,4-bis-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-butane-1,4-dione 
• 136570-25-7 (2R,4S,6R)-2-Bromo-4-((R)-2,2-dimethyl-4-phenyl-oxazolidine-3-carbonyl)-1,7-bis-((R)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-6-(2,2,2-trichloro-ethyl)-heptane-1,7-dione 
• 143668-81-9 (R)-1-((S)-2,2-Dimethyl-4-phenyl-oxazolidin-3-yl)-2-ethyl-pent-4-en-1-one 
• 143668-81-9 (S)-1-((S)-2,2-Dimethyl-4-phenyl-oxazolidin-3-yl)-2-ethyl-pent-4-en-1-one 

Relevant academic research and scientific papers

Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides

The use of carbonyl-stabilised ammonium ylides to access chiral glycidic amides and the corresponding aziridines has so far been limited to racemic trans-selective protocols. We herein report the development of an asymmetric approach to access such compou

Effective enantiocontrol in conjugate additions of organocuprates. Highly selective 1,5-chiral induction in the conjugate additions of cuprates to α,β-unsaturated amide derivatives of 2,2-dimethyloxazolidine chiral auxiliaries

α,β-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph2CuMgBrMgBrl is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,π* type charge transfer complexes.

Origins of stereoselectivity in radical additions: Reactions of alkenes and radicals bearing oxazolidine and thiazolidine amide groups

Single-crystal X-ray analysis of four alkenes that undergo stereoselective radical addition reactions are reported. The facial selectivity of radical additions to these alkenes is understood based upon their solid-state conformations. Alkenes which have a conformation placing a group at a position in space sterically protecting one of the faces from addition undergo radical addition with diastereofacial selectivity. The structures of the alkenes are analyzed by the polar coordinates of groups relative to the alkene center undergoing addition. The analysis of conformations of alkenes also provides a rationale for stereoselectivity in the reactions of radicals derived from the alkenes. Factors which influence the conformation of the alkene also apparently influence the conformation of analogous radicals. Several products of addition were also subjected to X-ray cryslallographic analysis, and the steric factors which influence the conformation of the reactant alkene are also observed to affect the conformation of the radical addition products.

Chiral auxiliary control of tacticity in free radical polymerization

Chiral oxazolidine acrylamides undergo stereocontrolled free radical polymerization. Remarkably high degrees of tacticity have been demonstrated in the polymerization of acrylamides with these chiral auxiliaries that are derived from valine, phenylglycine, and tert-leucine. The polyacrylamides formed in these polymerizations can be converted to poly(acrylic acid), P(AA), and poly(methyl acrylate), P(MA), by hydrolysis and esterification. Tacticities as high as 92% have been measured for P(AA) and P(MA) resulting from these reactions. NMR studies of the microstructure of the polymers formed using chiral auxiliaries to control the stereochemistry of the reaction showed that the distribution of stereochemical sequences could be predicted by a statistical analysis based upon the mechanism of stereoselection. Specifically, these studies confirm that the stereocontrol is the result of facial selectivity in the addition of the monomer to the growing polymer radical. This face selectivity is thought to be the result of steric hindrance to approach of the monomer to one face of the radical caused by the chiral auxiliary. Further NMR studies were used to propose an analysis of the stereochemistry of P(MA) at the hexad level. Using HETCOR techniques, eight of the twenty hexads were conclusively identified, and a further six were narrowed to two possible choices.

New chiral auxiliaries based on conformation control, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines. Synthesis and conformational analysis of acrylamide derivatives

New chirality-controlling auxiliaries, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines, are readily prepared from a C2-symmetric 1,2-ethanediamine and naturally occurring α-amino acids, respectively. Con

2,2-dimethyl-4-phenyloxazolidine and 2,2-dimethyl-4,5-diphenylimidazolidine as new chiral auxiliaries. Applications to asymmetric nitrile oxide cycloadditions

Asymmetric dipolar cycloadditions of a nitrile oxide to the acrylamide derivatives of two new chiral auxiliaries, (R)-2,2-dimethyl-4-phenyloxazolidines and (S,S)-2,2-dimethyl-4,5-diphenylimidazolidine, show satisfactorily high diastereoselectivities (up to 91%).