300592-70-5

Upstream product

• 113543-35-4 (4S)-3-((2S)-2-bromo-3-methylbutanoyl)-4-benzyl-1,3-oxazolidin-2-one 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 1177264-43-5 1-phenylsulfanyl-[1,2,4]-triazole 
• 300592-60-3 3-[(2R)-2-phenylthio-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one 

Downstream Products

• 1197375-26-0 (R)-1-[2-(phenylthio)-3-methylbutyl]-1H-imidazole 
• 1197375-24-8 (R)-(1-bromo-3-methylbutan-2-yl)(phenyl)sulfane 
• 300592-92-1 (2R,3R)-3-phenylthio-4-methylpentan-2-ol 
• 300592-82-9 (2S,3R)-3-phenylthio-4-methylpentan-2-ol 

Relevant academic research and scientific papers

Asymmetric Synthesis of Secondary Alcohols and 1,2-Disubstituted Epoxides via Organocatalytic Sulfenylation

Enantioenriched secondary alcohols can be prepared via a short reaction sequence involving asymmetric organocatalytic sulfenylation of an aldehyde, organometallic addition, and desulfurization. This process provides access to enantioenriched alcohols with sterically similar groups attached to the alcohol carbon atom. The intermediate β-hydroxysulfides can also serve as precursors to enantioenriched 1,2-disubstituted epoxides via alkylation of the sulfur and subsequent base-mediated ring closure.

Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions

A modular approach to the synthesis of a class of mixed phosphorus/sulfur ligands was designed to identify important ligand structural features for enantioselective palladium-catalyzed allylic subsitutions of acyclic and cyclic ayllic esters. After a systematic variation of the ligand substituents at sulfur, phosphorus, and the ligand backbone, ligand 11k was found to be optimal in the palladium-catalyzed allylic substitution of 1,3-diphenylpropenyl acetate with dimethyl malonate or benzylamine in high yield and excellent enantioselectivity (95-98% ee). A similar optimization of the mixed phosphorus/sulfur ligand for the palladium-catalyzed allylic substitution of cycloalkenyl acetates showed that 49g afforded the highest enantioselectivities (91-97% ee). Application of this methodology to heterocyclic substrates was developed as an efficient approach to the enantioselective synthesis of 3-substituted piperidines and dihydrothiopyrans. Models for asymmetric induction are discussed based on the absolute stereochemistry of the products, X-ray crystallographic data, and NMR spectroscopic data for relevant π-allyl complexes.