119163-36-9

Basic information

• Product Name: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide
• Synonyms: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide
• CAS NO: 119163-36-9
• Molecular Weight: 247.337
• Mol File: 119163-36-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide(119163-36-9)
• EPA Substance Registry System: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide(119163-36-9)

Safety Data

• Hazardous Substances Data: 119163-36-9(Hazardous Substances Data)

Upstream product

• 108-18-9 diisopropylamine 
• 7403-66-9 N,N-diisopropylchloroacetamide 
• 100-52-7 benzaldehyde 
• 23795-34-8 (E)-N,N-diisopropylcinnamamide 

Relevant articles and documents

Total regioselective and diastereospecific iodolysis of 2,3-epoxyamides promoted by SmI2: Synthesis of (2R*,3R*)- or (2R*,3S*)-2-hydroxy-3-iodoamides

The use of samarium diiodide as a source of iodides is reported. Thus, 2-hydroxy-3-iodoamides were obtained, with total regioselectivity, by treatment of 2,3-epoxyamides, in which the oxirane ring is 2,3-disubstituted or 2,2,3-trisubstituted, with SmI2. The ring-opening reaction was diastereospecific and (2R*,3R*)- or (2R*,3S*)-2-hydroxy- 3-iodoamides were obtained from cis- or trans-epoxyamides, respectively. The relative configuration of 2-hydroxy-3-iodoamides was established by X-ray analysis. A mechanism to explain this transformation has been proposed. The starting compounds 1 are easily prepared by the reaction of enolates derived from 2-chloroamides with aldehydes at -78°C.

A stereocontrolled approach to electrophilic epoxides

Lithium t-butyl hydroperoxide (easily generated by addition of an alkyl-lithium to anhydrous t-butyl hydroperoxide in THF solution) is a powerful reagent for the epoxidation of electrophilic alkenes at -20 to 0 °C under full stereocontrol. Thus αβ-unsaturated esters, sulphones, sulphoximines, and amides are readily epoxidised with complete regio- and stereo-specificity and with considerable chiroselectivity (20-100%) when appropriate chiral auxiliaries such as menthyl, 8-phenylmenthyl, or a camphor-sulphonamide derivative are used. Asymmetric αβ-unsaturated sulphoximines undergo epoxidation with 100% diastereoselectivity. The only exceptions to stereocontrol noted are heavily substituted maleate esters such as di-t-butyl maleate. The αβ-epoxy amides are shown to be valuable sources of the corresponding epoxy ketones by treatment with an organolithium, allowing a stereo- and chemoselective entry in high yield to these useful intermediates.