203176-56-1

Basic information

• Product Name: Oxazolidine, 4-phenyl-2-(trifluoromethyl)-, (2S,4R)-
• CAS NO: 203176-56-1
• Molecular Formula: C10H10F3NO
• Molecular Weight: 217.191
• Mol File: 203176-56-1.mol

Chemical Properties

• CAS DataBase Reference: Oxazolidine, 4-phenyl-2-(trifluoromethyl)-, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazolidine, 4-phenyl-2-(trifluoromethyl)-, (2S,4R)-(203176-56-1)
• EPA Substance Registry System: Oxazolidine, 4-phenyl-2-(trifluoromethyl)-, (2S,4R)-(203176-56-1)

Safety Data

• Hazardous Substances Data: 203176-56-1(Hazardous Substances Data)

Upstream product

• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 431-46-9 2,2,2-trifluoro-1-methoxy-ethanol 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 
• 1044222-31-2 (4R)-2-trifluoromethyl-4-phenyl-1,3-oxazolidine 
• 1428339-80-3 (2S,4R)-3-[(2R)-3-dibenzylamino-2-fluoropropanoyl]-4-phenyl-2-trifluoromethyloxazolidine 
• 1428339-77-8 (2S,4R)-3-[(2R)-2-fluoro-3-phenylpropanoyl]-4-phenyl-2-trifluoromethyloxazolidine 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 1026021-04-4 (2S,4R)-2-trifluoromethyl-4-phenyl-3-(3-(N,N-dibenzylamino)propanoyl)oxazolidine 
• 1220352-28-2 (2S,4R)-3-[(R)-2-benzyloxypropanoyl]-2-trifluoromethyl-4-phenyl-1,3-oxazolidine 
• 1220352-31-7 (2S,4R)-3-[(R)-2-benzyloxy-1-hydroxy-3-phenylpropyl]-2-trifluoromethyl-4-phenyl-1,3-oxazolidine 
• 1215007-33-2 (2S,4R)-3-[(2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-phenyl-2-trifluoromethyloxazolidine 
• 1026021-07-7 (2S,4R)-2-trifluoromethyl-4-phenyl-3-((2R)-3-(N,N-dibenzylamino)-2-benzylpropanoyl)oxazolidine 
• 904296-09-9 (2S,4R)-2-trifluoromethyl-3-[(S)-2-methyl-3-phenylpropanoyl]-4-phenyloxazolidine 

Downstream Products

• 1428339-73-4 (2S,4R)-4-phenyl-3-phenylacetyl-2-trifluoromethyloxazolidine 
• 1428339-76-7 (2S,4R)-3-[(2R)-2-fluoro-2-phenylacetyl]-4-phenyl-2-trifluoromethyloxazolidine 
• 1428339-74-5 (2S,4R)-hexanoyl-4-phenyl-2-trifluoromethyloxazolidine 
• 1428339-78-9 (2S,4R)-3-[(R)-2-fluorohexanoyl]-4-phenyl-2-trifluoromethyloxazolidine 

Relevant articles and documents

Asymmetric addition reactions of Grignard reagents to chiral fluoral hemiacetal: Asymmetric synthesis of 1-substituted-2,2,2-trifluoroethylamines

Asymmetric synthesis of 1-substituted-2,2,2-trifluoroethylamines is described starting from chiral fluoral hemiacetals derived from fluoral and (R)-phenylglycinol. The asymmetric addition reactions of Grignard reagents to the resultant imine are used in the key reaction step.

Synthesis of enantiopure trans-2,5-disubstituted trifluoromethylpyrrolidines and (2S,5R)-5-trifluoromethylproline

Enantiopure trans-2,5-disubstituted trifluoromethylpyrrolidines were prepared on a several gram scale starting from a readily available chiral fluorinated oxazolidine (Fox). A pure oxazolopyrrolidine intermediate could be obtained after an efficient separ

Crystallization-induced dynamic resolution of fox chiral auxiliary and application to the diastereoselective electrophilic fluorination of amide enolates

A highly efficient crystallization-induced dynamic resolution (CIDR) of trans-Fox (fluorinated oxazolidine) chiral auxiliary is reported. This chiral auxiliary was used for highly diastereoselective (>98% de) electrophilic fluorination of amide enolates. After removal of the chiral auxiliary, highly valuable enantiopure α-fluorocarboxylic acids and β-fluoroalcohols are obtained.

Highly diastereoselective α-hydroxylation of fox chiral auxiliary-based amide enolates with molecular oxygen

"Figure Presented" Using a trifluoromethylated oxazolidine (Fox) chiral auxiliary, the hydroxylation reaction of enolates was very efficiently performed under smooth and friendly conditions with molecular oxygen as oxidizer. This reaction occurred with an extremely high diastereoselectivlty. After cleavage, the chlral auxiliary Is efficiently recovered and highly valuable enantlopure oxygenated carboxylic acids and alcohols are released.

Asymmetric aldol reactions using chiral CF3-Oxazolidines (Fox) as chiral auxiliary

The aldol reactions of amide enolates derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur in good yields with a moderate anti diastereoselectivity (Li and Na enolates) to a high syn diastereoselectivity (boron enolate). After remov

Highly diastereoselective synthetic route to enantiopure β2-amino acids and γ-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary

(Chemical Equation Presented) The alkylation reactions of an amide enolate derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur with a complete diastereoselectivity and in good yields with various electrophiles. This reaction provid

Convenient asymmetric synthesis of β-trifluoromethyl-β-amino acid, β-amino ketones, and γ-amino alcohols via Reformatsky and Mannich-type reactions from 2-trifluoromethyl-1,3-oxazolidines

The stereoselective syntheses of β-trifluoromethyl-β-amino ester, β lactams, and β-amino ketones starting from an oxazolidine derived from trifluoroacetaldehyde hemiacetal and (R)-phenylglycinol are reported. The Mannich-type reaction involving a chiral f

Chiral 4-phenyl-2-trifluoromethyloxazolidine: A high-performance chiral auxiliary for the alkylation of amides

(Chemical Equation Presented) A bit on the side: Extremely high diastereoselectivities (> 99% de) were attained in the α-alkylation and -allylation of amides by using a trifluoromethylated (sphere) oxazolidine as a chiral auxiliary. Reductive cleavage of the amide bond led to the recovery of this fluorinated chiral auxiliary in high yield.