331258-65-2

Upstream product

• 214477-57-3 (+)-(3R,4S)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-phenoxy-1-(2-propen-yl)-2-azetidinone 
• 214477-58-4 (3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-phenoxy-1-allylazetidin-2-one 
• 701-99-5 Phenoxyacetyl chloride 

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.