320606-12-0

Basic information

• Product Name: 2-Oxazolidinone, 5,5-dimethyl-3-(1-oxobutyl)-4-(phenylmethyl)-, (4S)-
• CAS NO: 320606-12-0
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Mol File: 320606-12-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 5,5-dimethyl-3-(1-oxobutyl)-4-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 5,5-dimethyl-3-(1-oxobutyl)-4-(phenylmethyl)-, (4S)-(320606-12-0)
• EPA Substance Registry System: 2-Oxazolidinone, 5,5-dimethyl-3-(1-oxobutyl)-4-(phenylmethyl)-, (4S)-(320606-12-0)

Safety Data

• Hazardous Substances Data: 320606-12-0(Hazardous Substances Data)

Upstream product

• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 320606-07-3 (S)-3-(2'-benzyl-3'-phenylpropionyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 141-75-3 butyryl chloride 
• 168297-85-6 (S)-4-benzyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 168297-85-6 (S)-4-benzyl-5,5-dimethyloxazolidin-2-one 

Relevant articles and documents

Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.

SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes

The proclivity of α-branched N-2′-benzyl-3′-phenylpropionyl derivatives of (S)-4-benzyl-5,5-dimethyl-, (S)-4-phenyl-5,5-dimethyl-, (S)-4-isopropyl-5,5-dimethyl-, (S)-4-benzyl- and (S)-4-benzyl-5,5-diphenyl-oxazolidin-2-ones to generate directly 2-benzyl-3-phenylpropionaldehyde upon hydride reduction with DIBAL is investigated. The (S)-4-benzyl-5,5-dimethyl-derivative proved optimal for inhibition of endocyclic nucleophilic attack, giving 2-benzyl-3-phenylpropionaldehyde in good yield upon reduction. Application of this methodology for the asymmetric synthesis of chiral aldehydes via diastereoselective enolate alkylation of a range of (S)-N-acyl-4-benzyl-5,5-dimethyloxazolidin-2-ones to afford an array of α-substituted-N-acyl-5,5-dimethyloxazolidin-2-ones (85-94% de) and subsequent reduction with DIBAL afforded directly non-racemic α-substituted aldehydes without loss of stereochemical integrity (87-94% ee). The extension of this protocol for the asymmetric synthesis of β-substituted aldehydes is demonstrated, via the diastereoselective conjugate addition of a range of organocuprates to (S)-N-acyl-4-phenyl-5,5-dimethyloxazolidin-2-ones which proceeds with high diastereoselectivity (generally >95% de). Reduction of the conjugate addition products with DIBAL gives non-racemic β-substituted aldehydes in high yields and in high ee (generally >95% ee). This methodology is exemplified by the asymmetric synthesis of (R)-3-isopropenylhept-6-enal, which has previously been used in the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromones of the California red scale.