931385-40-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 1285721-47-2 C₂₄H₂₉NO₅S 
• 1285721-29-0 C₁₉H₂₇NO₄S 
• 1195778-44-9 C₁₈H₂₅NO₄S 
• 154006-98-1 (4S)-3-<(2E)-3-(4-methoxyphenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 931385-32-9 anti-(4S,2'S,3'S)-3-[2'-bromo-3'-hydroxy-3'-(4-methoxyphenyl)-propionyl]-4-benzyloxazolidin-2-one 

Downstream Products

• 220736-25-4 (4R,5R)-cytoxazone 
• 383420-35-7 (2R,3R)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1,2-propanediol 
• 237736-22-0 (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol 

Relevant academic research and scientific papers

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides

Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric epoxy alcohols depending on which of the sulfonium salts, prepared from L-amino acids (6 and 9 from L-valine or 15 and 16 from L-serine) was employed.

A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide

A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.

NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (-)-cytoxazone and droxidopa

The NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral α-bromo-β-hydroxy carboxamides. Excellent