876609-55-1

Upstream product

• 136458-56-5 2,3-bis((benzyloxy)methyl)oxirane 
• 98-88-4 benzoyl chloride 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 81177-24-4 (S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane 

Downstream Products

• 134964-78-6 (2R,3R)-1-((2S,3S)-2,3-Bis-benzyloxymethyl-aziridin-1-yl)-3-hydroxy-2-methyl-3-phenyl-propan-1-one 
• 134964-69-5 1-((2S,3S)-2,3-Bis-benzyloxymethyl-aziridin-1-yl)-propan-1-one 
• 134964-68-4 (2S,3S)-2,3-Bis-benzyloxymethyl-aziridine 
• 134964-70-8 (R)-1-((2S,3S)-2,3-Bis-benzyloxymethyl-aziridin-1-yl)-2-methyl-3-phenyl-propan-1-one 

Relevant academic research and scientific papers

On the use of C2-symmetric aziridines as chiral auxiliaries

A systematic study has been made of the utility of readily available C2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the axuiliaries can be cleaved off non-destructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

Chemoenzymatic route to stereodefined 2-(azidophenyl)oxazolines for click chemistry

Aryl-substituted esters of a racemic diprotected 2-azido-1-alkanol were submitted to the Staudinger/aza-Wittig reaction in order to assess scope and establish conditions for their cyclization to the corresponding 2,4,5-trisubstituted oxazolines. Following