869856-47-3

Upstream product

• 1439-07-2 (R,R)-trans-stilbene epoxide 
• 1269141-77-6 (1R,4R,5R,6R)-6-benzyl-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octan-6-ium trifluoromethanesulfonate 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1146729-43-2 syn-1-(2-bromophenyl)-2-phenylethane-1,2-diol 
• 1024916-46-8 diethyl ((R)-phenyl{2-[(2R,3R)-3-phenyloxiran-2-yl]phenyl}methyl)malonate 

Relevant academic research and scientific papers

A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides.

Michael addition of ortho-lithiated aryloxiranes to α,β- unsaturated malonates: Synthesis of tetrahydroindenofuranones

A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.