212378-97-7

Basic information

• Product Name: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide
• Synonyms: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide
• CAS NO: 212378-97-7
• Molecular Weight: 223.339
• Mol File: 212378-97-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide(212378-97-7)
• EPA Substance Registry System: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide(212378-97-7)

Safety Data

• Hazardous Substances Data: 212378-97-7(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 
• 146374-27-8 S-tert-butylsulfinimide 
• 1826-67-1 vinyl magnesium bromide 
• 1172578-24-3 C₁₂H₁₆ClNOS 
• 350-03-8 methyl-3-pyridylketone 

Downstream Products

• 1373154-77-8 (R)-4,4,4-trifluoro-3-hydroxy-1,3-diphenylbutan-1-one 
• 1426585-76-3 pinacol (R)-1-N-sulfinylphenylmethyl-1-boronate 
• 1426585-77-4 pinacol (R)-1-N-sulfinylphenylmethyl-1-boronate 
• 131154-18-2 (R)-(1-methyl-1-phenyl-but-3-enyl)amine 
• 131154-23-9 N-((R)-1-Methyl-1-phenyl-but-3-enyl)-acetamide 
• 1585970-62-2 C₁₉H₂₆N₂O₃S 
• 20826-48-6 (R)-N-(1-phenylethyl)benzamide 
• 1354630-29-7 (Rs,1S,3R)-N-((E)-3-hydroxy-1,5-diphenyl-3-(trifluoromethyl)pent-4-enyl)tert-butanesulfinamide 
• 1354630-26-4 (Rs,R)-N-((E)-5-(4-chlorophenyl)-3-hydroxy-1-phenyl-3-(trifluoromethyl)pent-4-enylidene)tert-butanesulfinamide 

Relevant articles and documents

Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines

The direct preparation of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41-90%), with relatively rapid reaction times (4-15 hours); their synthetic application was examined through the reaction with the yl

Racemization free protocol for the synthesis of N - Tert -butanesulfinyl ketimines

Figure presented. A general and robust racemization-free protocol for the synthesis of a variety of N-tert-butanesulfinyl ketimines is reported. Reaction progress was monitored by 1H NMR using the nonperturbing internal standard diglyme, and ke

Transition-Metal-Free Hydrogen Autotransfer: Diastereoselective N-Alkylation of Amines with Racemic Alcohols

A practical method for the synthesis of α-chiral amines by alkylation of amines with alcohols in the absence of any transition-metal catalysts has been developed. Under the co-catalysis of a ketone and NaOH, racemic secondary alcohols reacted with Ellman's chiral tert-butanesulfinamide by a hydrogen autotransfer process to afford chiral amines with high diastereoselectivities (up to >99:1). Broad substrate scope and up to a 10 gram scale production of chiral amines were demonstrated. The method was applied to the synthesis of chiral deuterium-labelled amines with high deuterium incorporation and optical purity, including examples of chiral deuterated drugs. The configuration of amine products is found to be determined solely by the configuration of the chiral tert-butanesulfinamide regardless of that of alcohols, and this is corroborated by DFT calculations. Further mechanistic studies showed that the reaction is initiated by the ketone catalyst and involves a transition state similar to that proposed for the Meerwein–Ponndorf–Verley (MPV) reduction, and importantly, it is the interaction of the sodium cation of the base with both the nitrogen and oxygen atoms of the sulfinamide moiety that makes feasible, and determines the diastereoselectivity of, the reaction.

Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-Butylsulfinyl)imines

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