251480-07-6

Basic information

• Product Name: (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone
• Synonyms: (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone
• CAS NO: 251480-07-6
• Molecular Weight: 327.38
• Mol File: 251480-07-6.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(251480-07-6)
• EPA Substance Registry System: (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(251480-07-6)

Safety Data

• Hazardous Substances Data: 251480-07-6(Hazardous Substances Data)

Upstream product

• 331258-76-5 (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone 
• 701-99-5 Phenoxyacetyl chloride 
• 78-94-4 methyl vinyl ketone 
• 251480-04-3 (+)-(2R,3R)-1-(4-pentynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde 

Relevant articles and documents

Diastereoselective Baylis-Hillman reaction of 4-oxoazetidine-2-carbaldehydes: Rapid, stereocontrolled and divergent radical synthesis of highly functionalised β-lactams fused to medium rings

Baylis-Hillman adducts derived from enantiopure 1-alkenyl- or alkynyl-4-oxoazetidine-2-carbaldehydes are used for the stereoselective and divergent preparation of highly functionalised β-lactams fused to medium rings through novel, chemocontrolled tandem radical addition-cyclization sequences.

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.