353494-53-8

Upstream product

• 221909-59-7 (+)-(3R,4R)-4-formyl-3-allyloxy-1-(p-methoxyphenyl)-2-azetidinone 
• 292638-85-8 acrylic acid methyl ester 
• 814-68-6 acryloyl chloride 
• 353494-43-6 (2S,4S,5R)-5-[(2S,3R)-3-Allyloxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-2-methyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of unusual fused tricyclic β-lactam structures via aza-cycloadditions/ring closing metathesis

Conveniently substituted bis-β-lactams, pyrrolidinyl-β-lactams, and piperidinyl-β-lactams undergo ring-closing methatesis using Grubbs' carbene, Cl2(Cy3P)2Ru=CHPh, to give medium-sized rings fused to bis-2-azetidinone, pyrrolidinyl-2-azetidinone, or piperidinyl-2-azetidinone systems. The diolefinic cyclization precursors can be obtained from optically pure 4-oxoazetidine-2-carbaldehydes bearing an extra alkene tether at position 1 or 3 of the β-lactam ring via [2 + 2] cycloaddition of imino 2-azetidinones, N-metalated azometine ylide [3 + 2] cycloaddition, and subsequent N-acylation of the pyrrolidinyl nitrogen atom, or through aza-Diels-Alder cycloaddition of 2-azetidinone-tethered imines. Under standard reaction conditions, the combination of cycloaddition reactions of 2-azetidinone-tethered imines with ring-closing methatesis offers an asymmetric entry to a variety of unusual fused tricyclic 2-azetidinones bearing two bridgehead nitrogen atoms.

Unusual fused tricyclic 2-azetidinones: Stereocontrolled synthesis of rigid dipeptide surrogates from β-lactam-tethered imines via sequential cycloaddition/ring-closing metathesis

The combination of [3+2] and [2+2] cycloaddition reactions of 2-azetidinone-tethered imines with ring-closing methatesis offers an asymmetric entry to a variety of unusual fused tricyclic 2-azetidinones bearing a bridgehead nitrogen atom, related to confo