163065-94-9

Upstream product

• 108-30-5 succinic acid anhydride 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 

Downstream Products

• 612806-16-3 methyl [(S)R]-4-oxo-5-(p-tolylsulfinyl)pentanoate 
• 612806-20-9 [4R,(S)R]-4-hydroxy-1-phenyl-5-(p-tolylsulfinyl)pentanone 
• 612806-27-6 [2S,5R,(S)R]-2-phenyl-5-[(p-tolylsulfinyl)methyl]tetrahydrofuran 
• 612806-18-5 [4R,(S)R]-N-methoxy-N-methyl-4-hydroxy-5-(p-tolylsulfinyl)pentanamide 
• 612806-17-4 methyl [4R,(S)R]-4-hydroxy-5-(p-tolylsulfinyl)pentanoate 
• 612806-21-0 [5R,(S)R]-5-hydroxy-6-(p-tolylsulfinyl)hexan-2-one 
• 612806-35-6 [2R,6R,(S)R]-2-methyl-5-[(p-tolylsulfinyl)methyl]tetrahydrofuran 
• 612806-30-1 (2S,5R)-2-phenyl-5-(hydroxymethyl)tetrahydrofuran 
• 163066-01-1 (R)-5-Hydroxy-6-((R)-toluene-4-sulfinyl)-hexanoic acid 

Relevant academic research and scientific papers

Reductive cyclizations of hydroxysulfinyl ketones: Enantioselective access to tetrahydropyran and tetrahydrofuran derivatives

The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (-)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).

Enantioselective Synthesis of γ- and δ-Lactones

The synthesis of enantiomerically pure sulfinyl oxoacids HO2CCH2(CH2)nCOCH(R)SOTol (n = 1 and 2, R = H, CH3), and their stereoselective reduction with DIBAL catalysed by ZnBr2 are reported.The resulting hydroxysulfoxides were cyclized in situ u