131233-89-1

Basic information

• Product Name: 4-Oxazolidinecarboxylicacid, 2-(1,1-dimethylethyl)-3-formyl-, methyl ester, (2S,4R)-
• Synonyms: 4-Oxazolidinecarboxylicacid, 2-(1,1-dimethylethyl)-3-formyl-, methyl ester, (2S-cis)-
• CAS NO: 131233-89-1
• Molecular Formula: C10H17 N O4
• Molecular Weight: 215.25
• Product Categories: Chiral Reagents;Heterocycles;Chiral Reagents, Heterocycles
• Mol File: 131233-89-1.mol

Chemical Properties

• Appearance: /
• Solubility: Acetone, Dichloromethane, Ethyl Acetate,
• CAS DataBase Reference: 4-Oxazolidinecarboxylicacid, 2-(1,1-dimethylethyl)-3-formyl-, methyl ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolidinecarboxylicacid, 2-(1,1-dimethylethyl)-3-formyl-, methyl ester, (2S,4R)-(131233-89-1)
• EPA Substance Registry System: 4-Oxazolidinecarboxylicacid, 2-(1,1-dimethylethyl)-3-formyl-, methyl ester, (2S,4R)-(131233-89-1)

Safety Data

• Hazardous Substances Data: 131233-89-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 93250-90-9 (2S,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 2258-42-6 formyl acetic anhydride 
• 190080-34-3 (2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 93250-89-6 methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate 
• 630-19-3 pivalaldehyde 

Downstream Products

• 93250-99-8 (2R,4R)-2-tert-Butyl-3-formyl-4-(hydroxy-phenyl-methyl)-oxazolidine-4-carboxylic acid methyl ester 

Relevant articles and documents

Isolation and X-ray structures of reactive intermediates of organocatalysis with diphenylprolinol ethers and with imidazolidinones a survey and comparison with computed structures and with 1-acyl-imidazolidinones: The 1,5-repulsion and the geminal-diaryl

Reaction of 2-phenylacetaldehyde with the Me3Si ether of diphenyl-prolinol, with removal of H2O, gives a crystalline enamine (1). The HBF4 salts of the MePh2Si ether of diphenyl-prolinol and of 2-(tert-butyl)-3-

Stereoselective Alkylierung an C(α) von Serin, Gycerinsaeure, Thereonin und Weinsaeure ueber heterocyclische Enolate mit exocyclischer Doppelbindung

The chiral, non-racemic title acids are converted to methyl dioxalene- (cf. 13), oxazoline- (4) and oxazolidine-carboxylates (cf. 9).Deprotonation by Li(i-Pr)2N at dry-ice temperature gives solutions of the litium enolates A-D with exocyclic enolate double bonds.These are stable enough with respect to β-elimination (Scheme 1) to be alkylated with or without cosolvents such as HMPA or DMPU.The products are formed in good to excellent yields and, with the exception of the tartrate derived acetonide (see Schemem 2), with diastereoselectivities above 90percent.While the tartrate- and threonine-derived enolates (A and B, resp.) are chiral due to the second stereogenic center of the precursors, the serine- and glyceric-acid-derived enolates are non-racemic due to a tert butyl-substituted (pivalaldehyde-derived) acetal center (C and D, resp.).The products of alkylation can be hydrolyzed to give α-branched tartaric acid (Scheme 2), allothreonine (Scheme 3), serine (Scheme 4), and glycerine-acid derivatives (Scheme 5) with quaternary stereogenic centers.The configurations of the products are determined by NOE-NMR measurements and by chemical correlation.These show taht the dioxolane-derived enolates A and D are alkylated preferentially from that face of the ring which is alredy substituted ('syn'-attack).The 'syn'-attack is postulated to arise from strong folding of the heterocyclic ring due to elelctronic repulsion between the enolate ?-system and non-bonding elelctron pairs on the heteroatoms (see Scheme 6).

α-ALKYLATION OF SERINE WITH SELF-PRODUKTION OF THE CENTER OF CHIRALITY

The lithium enolate 6 of methyl (2R,4S)-2-t-butyl-3-formyl-oxazolidine-4-carboxylate (4b) derived from (S)-(+)-serine can be generated with LDA in THF solution at -75 deg C.Alkylations (9) and hydroxyalkylations (10,11) occur preferentially (>95:5) from the Re-face of the donor center (relative topicity lk).This stereochemical course is derived from the absolute configuration of 2-deuterio- and 2-methyl-serine (12,13) obtained through the enolate 6.