187986-91-0

Upstream product

• 187986-87-4 (1R,5S)-3-Ethoxy-5-((S)-toluene-4-sulfinyl)-cyclopent-2-enol 
• 187986-85-2 (S)-3-Ethoxy-5-((S)-toluene-4-sulfinyl)-cyclopent-2-enone 
• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 187986-90-9 (1S,2R,5S)-3,3-Diethoxy-2-iodo-5-((S)-toluene-4-sulfinyl)-cyclopentanol 

Downstream Products

• 187986-94-3 (S)-5,5-Diethoxy-3-(toluene-4-sulfonyl)-cyclopent-2-enol 
• 187986-92-1 (S)-5,5-Diethoxy-3-((R)-toluene-4-sulfinyl)-cyclopent-2-enol 

Relevant academic research and scientific papers

Sulfoxide-mediated asymmetric synthesis of glycosidase inhibitor precursors

The highly diastereoselective DIBALH and DIBALH/ZnBr2 reduction of enantiomerically pure (5S,(S)S)-3-ethoxy-5-(p-tolylsulfinyl)cyclopentenone (9)is used as a key step to the synthesis of oxazolidinone 2, a precursor of glycosidase inhibitor mannostatin. Compound 9 was obtained from 3-ethoxycyclopentenone by direct sulfinylation with (S)-N-benzyl-N-(p-tolylsulfinyl)propionamide.

Regio- and stereocontrolled formation of chiral epoxy oxazolidines via bromocarbamation of N-Boc alkenyl oxazolidines. Application to asymmetric synthesis

Treatment of α-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide on these epoxides, followed by a few functional group manipulations, eventually affords chiral β-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.