168298-08-6

Basic information

• Product Name: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one
• Synonyms: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one
• CAS NO: 168298-08-6
• Molecular Weight: 321.376
• Mol File: 168298-08-6.mol

Chemical Properties

• CAS DataBase Reference: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one(168298-08-6)
• EPA Substance Registry System: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one(168298-08-6)

Safety Data

• Hazardous Substances Data: 168298-08-6(Hazardous Substances Data)

Upstream product

• 110480-87-0 (R)-1-amino-2-methyl-1-phenyl-propan-2-ol 
• 102-92-1 Cinnamoyl chloride 
• 170918-42-0 (R)-(-)-5,5-dimethyl-4-phenyl-2-oxazolidinone 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 875-74-1 (R)-phenylglycine 
• 100-52-7 benzaldehyde 
• 102-92-1 cinnamoyl chloride 
• 170918-36-2 (R)-3-(2',2'-dimethyl-1'-oxopropyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 170918-35-1 N-<(1R)-2-hydroxy-2-methyl-1-phenylpropyl>-2,2,2-trichloroethanamide 
• 168298-07-5 (4R)-3-<2'(E)-butenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 1253181-42-8 (R)-3-(2,3-dibromo-3-phenylpropanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 

Relevant articles and documents

Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described.

Studies on the synthesis and dynamic NMR properties of 2-(benzylidene amino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl]acetamide

An efficient method was employed for the preparation of 2-(benzylideneamino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl] acetamide utilizing optically pure (R)-5,5-dimethyl-4-phenyloxazolidin-2-one. This product showed interesting dynamic NMR properties for

Synthesis of the chiral α,β-unsaturated N-acyl-oxazolidin-2-ones by wittig reaction

A new, universal, and versatile method has been developed for the synthesis of the chiral α,β-unsaturated N-acyl-oxazolidin-2-ones 4 based on the Wittig reaction of the triphenylphosphonium salt 7 derived from the (R)-3-(2-Chloro-acetyl)-5,5-dimethyl-4-ph

The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B.

(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D- phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (-)-Aplysillamide B.

Chiral auxiliaries

This invention relates to novel compounds of general formula (I): STR1 wherein the two R1 groups are identical lower alkyl groups or together form a lower alkylene group; R2 and R3 are both different and are selected from hydrogen atoms or organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R2 and R3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form. The compounds are useful chiral auxiliaries to which a wide range of, for example, acyl groups containing prochiral centers may be readily and reversibly coupled to the 3-position amino group.