251480-03-2

Upstream product

• 701-99-5 Phenoxyacetyl chloride 
• 331258-73-2 (+)-(3R,4S)-1-(3-butynyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenoxy-2-azetidinone 

Downstream Products

• 251480-06-5 (3R,4S)-1-(3-butynyl)-4-[(R)-1-hydroxy-2-methylidene-3-oxo-butyl]-3-phenoxy-2-azetidinone 
• 1026247-61-9 C₁₅H₁₆N₂O₃ 

Relevant academic research and scientific papers

Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes

DABCO promoted reactions of various activated vinyl systems with optically pure 4-oxoazetidine-2-carbaldehydes 1 gave rise to Baylis - Hillman adducts 3 with excellent syn stereoselectivities, without detectable racemization. Products 3 are used for the asymmetric preparation of unusual 2-azetidinones fused to medium-sized rings via chemo- and stereocontrolled divergent radical cyclization. The formation of bicyclic β-lactams 4 - 6 could be rationalized through a tandem radical Michael addition/endo cyclization or a tandem radical addition/Michael addition, depending on the electronic nature of the radical promoter.

Reverse-Cope elimination versus 1,3-dipolar cycloaddition in the reaction of enantiopure 2-azetidinone-tethered alkynylaldehydes with N- methylhydroxylamine

Enantiopure 2-azetidinone-tethered alkynylaldehydes 1 react stereoselectively under mild conditions with N-methylhydroxylamine to yield products derived from either intramolecular reverse-Cope elimination or 1,3- dipolar cycloaddition, depending on both t