392668-05-2

Upstream product

• 199847-19-3 (R)-3-Phenyl-3-(2-trimethylsilanyl-phenylsulfanyl)-propionic acid methyl ester 
• 108-98-5 thiophenol 
• 83620-45-5 (2E)-3-phenyl-1-(1H-pyrazol-1-yl)prop-2-en-1-one 
• 103-26-4 methyl cinnamate 
• 33356-45-5 2-(Trimethylsilyl)benzenethiol 

Downstream Products

• 138098-75-6 (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate 

Relevant academic research and scientific papers

Catalytic Enantioselective Synthesis of Protecting-Group-Free 1,5-Benzothiazepines

A one-pot enantioselective route to N-unprotected 2,3-dihydro-1,5-benzothiazepinones, by an organocatalyzed sulfa-Michael reaction of readily available α,β-unsaturated N-acyl pyrazoles with 2-aminothiophenols followed by silica-gel-catalyzed lactamization

Chiral amino ether-controlled catalytic enantioselective arylthiol conjugate additions to α,β-unsaturated esters and ketones: Scope, structural requirements, and mechanistic implications

Asymmetric conjugate addition reaction of 2-trimethylsilylbenzenethiol with enoates and enones is catalyzed by a chiral amino ether-lithium thiolate complex and affords adducts with high enantioselectivity. Both the s-cis conformation and a steric wall at one side of the carbonyl group are structural requirements in substrates yielding adducts with high enantioselectivity. Reactions with tert-butyl enones gave addition products with high enantioselectivity. Construction of two contiguous chiral centers was possible by this addition-protonation sequence. Methyl tiglate was stereoselectively converted to a single syn-adduct of 95% enantiomeric excess (ee) bearing two contiguous chiral centers. Methyl 2-phenyl-2-butenoate was converted to a single syn-adduct of 95% ee, which was desulfurized to methyl 2-phenylbutanoate of 95% ee. These additions generate a transient lithium enolate that is protonated by a thiol anti to the C-S bond, giving the corresponding product having two adjacent stereocenters.