337522-48-2

Upstream product

• 103588-86-9 4-benzyloxycarbonyl-1-t-butyldimethylsilyl-2-azetidinone 
• 63226-81-3 1-phenylmethyl-2-hydroxymethylaziridine 
• 21384-53-2 methyl 1-benzylaziridine-2-carboxylate 
• 100-46-9 benzylamine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-39-0 benzyl bromide 
• 188304-74-7 (R,S) 1-(t-butyldimethylsilyl)-4-(hydroxymethyl)-2-azetidinone 

Downstream Products

• 85390-46-1 1-Benzyl-4-(hydroxymethyl)azetidin-2-one 

Relevant academic research and scientific papers

Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone

The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78°C into amide anion by N-O migration of the silyl protecting group. The occurrence of this intermediate was proved by quenching with benzyl bromide and phenethyl chloroformate, giving respectively N-benzyl (4) and N-(phenethyloxycarbonyl) (6) derivatives of 4-(t-butyldimethylsilyloxy)methyl-2-azetidinone.

On the effect of ring substituents in the carbonylation of aziridines

The effect of ring substituents on the cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to β-lactams has been investigated. A variety of aziridines with different substituents and stereochemistry has been synthesized and subjected to carbonylation. The ring expansion to β-lactam takes place in the absence of an electron-withdrawing substituent and higher yields are always obtained for cis-aziridines. Moreover, the regioselectivity of the reaction is affected by the nature of substituents at ring carbon atoms.