224433-96-9

Basic information

• Product Name: [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester
• Synonyms: [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester
• CAS NO: 224433-96-9
• Molecular Weight: 393.507
• Mol File: 224433-96-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester(224433-96-9)
• EPA Substance Registry System: [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester(224433-96-9)

Safety Data

• Hazardous Substances Data: 224433-96-9(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 224433-92-5 (S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethylamine 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 100-52-7 benzaldehyde 
• 121411-08-3 (4-Methoxy-phenyl)-[(S)-1-phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 

Downstream Products

• 20989-17-7 (2S)-2-phenylglycinol 
• 130406-31-4 benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate 

Relevant articles and documents

Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction

The results presented in this paper demonstrate that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) is a function of a) the reaction conditions used and b) the electronic properties of the arylidene moiety on the starting imine. High kinetically controlled (2S,R(S)) diastereoselectivity (-70 °C) was achieved for additions of imines bearing relatively electron-rich N-arylidene groups, while an electron-deficient nature of this group was found to favor the opposite stereochemical outcome. On the other hand, the reactions run under thermodynamically controlled conditions (0 °C) afforded equimolar mixtures of the diastereomeric products regardless of the pattern of substitution on the starting imines. Enantiopure α-arylglycinols were readily synthesized by 'non-oxidative' Pummerer rearrangement of diastereomerically pure β-aryl-β-N-(acyl)aminoalkyl sulfoxides, prepared from the corresponding N-PMP derivatives.