873692-52-5

Upstream product

• 2645-02-5 methyl tosylglycinate 
• 873692-64-9 N-(4-methylphenylsulfonyl)-N-2-propen-1-ylglycinemethyl ester 
• 361459-74-7 4-methyl-N-(2-oxoethyl)-N-2-propen-1-ylbenzenesulfonamide 

Downstream Products

• 873692-57-0 N-allyl-N-(toluene-4-sulfonyl)-2-aminoacetaldehyde O-tert-butyldimethylsilyloxime 

Relevant academic research and scientific papers

Intramolecular cycloaddition of O-tert-butyldimethylsilyloximes in the presence of BF3-OEt2

Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3·OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.