41339-39-3

Upstream product

• 108-94-1 cyclohexanone 
• 6362-63-6 ethyl 3-cyano-3-phenylpyruvate 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 84863-93-4 3-hydroxy-4-phenyl-1H-pyrrole-2,5-dione 
• 397886-95-2 5-(2-bromo-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

CYCLOCONDENSATION OF β-OXONITRILES WITH KETONES OR ALDEHYDES

β-Oxonitriles (1) are easily condensed with cyclic ketones (2a-e) in anhydrous strong acidic conditions to give 1-oxa-5-azaspiroundec-2-en-4-ones (3a-e).In the same manner acyclic ketones (2f,g) or aldehydes (2h,i) afford 2,3-dihydro-4H-1,3-oxazin-4-

2,3-Dihydro-4H-1,3-oxazin-4-ones, novel auxiliaries for the stereoselective synthesis of 1β-methylcarbapenems

Dihydrooxazinones 9, prepared from benzylcyanide in two steps serve as efficient auxiliaries for the stereoselective synthesis of β-methylcarbapenem intermediate 2. Reformatsky-type reactions of 4-acetoxyazetidinone with α-bromopropionyl dihydrooxazinone 10 provided β-methylazetidinones 4 in high diastereoselectivities. The auxiliaries 9 were also easily removed in the Dieckmann cyclization leading to β-methylcarbapenem skeletons. Practical synthesis of β-methylenolphosphates 2 from 4-acetoxyazetidinone 3 was achieved in three steps (61-77% overall yield).