1426585-64-9

Basic information

• Product Name: (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine
• Synonyms: (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine
• CAS NO: 1426585-64-9
• Molecular Weight: 223.339
• Mol File: 1426585-64-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine(CAS DataBase Reference)
• NIST Chemistry Reference: (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine(1426585-64-9)
• EPA Substance Registry System: (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine(1426585-64-9)

Safety Data

• Hazardous Substances Data: 1426585-64-9(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 1587692-41-8 (R,R_S)-N-(tert-butylsulfinyl)-3-amino-4-phenylbutan-2-one 

Relevant articles and documents

Stereoselective Synthesis of 2-(2-Aminoalkyl)- and 1,3-Disubstituted Tetrahydro-1H-pyrido[4,3-b]- Benzofuran and Indole Derivatives

The addition of an allenyl indium intermediate to chiral N-tert-butanesulfinyl imines 7 proceeds with high levels of diastereocontrol. The resulting homopropargylic amine derivatives 10 were transformed into 2-(2-aminoalkyl)benzofuran and indole derivatives 13 and 19, after Sonogashira coupling with o-iodophenol or o-iodoaniline, followed by formation of the heteroaromatic ring through an intramolecular cyclization. Enantioenriched tetrahydropyrido-benzofuran and indole derivatives 16 and 21 were prepared through a Pictet-Spengler condensation of the free amines derived from compounds 15 and 20, involving the nucleophilic 3-position of the benzofuran or indole moiety.

One-Pot Synthesis of N-tert-Butylsulfinylimines and Homoallylamine Derivatives from Epoxides

The reaction of epoxides with tert-butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride–diethyl ether, in THF as solvent, under microwave or thermal activation, produces N-tert-butylsulfinylimines in reasonable yields. Aromatic and gem-disubstituted and trisubstituted alkyl epoxides performed better than mono-alkyl-substituted compounds. After imine formation, a subsequent indium-promoted allylation can be carried out in the same reaction flask in a single synthetic operation leading to homoallylamine derivatives with generally high yields.

Indium-promoted diastereo- and regioselective propargylation of chiral sulfinylimines

The reaction of different chiral imines 3 derived from aldehydes or ketones with the silylated propargyl bromide 4b under sonication in the presence of indium metal led mainly or exclusively to the formation of protected homopropargylamines 5 in a diaster