307002-99-9

Basic information

• Product Name: (4R,5R,6S)-6-Ethoxymethoxy-4-(phenylsulfonyl)bicyclo[3.3.0]oct-1-en-3-one
• Synonyms: (4R,5R,6S)-6-Ethoxymethoxy-4-(phenylsulfonyl)bicyclo[3.3.0]oct-1-en-3-one
• CAS NO: 307002-99-9
• Molecular Weight: 336.409
• Mol File: 307002-99-9.mol

Chemical Properties

• CAS DataBase Reference: (4R,5R,6S)-6-Ethoxymethoxy-4-(phenylsulfonyl)bicyclo[3.3.0]oct-1-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R,6S)-6-Ethoxymethoxy-4-(phenylsulfonyl)bicyclo[3.3.0]oct-1-en-3-one(307002-99-9)
• EPA Substance Registry System: (4R,5R,6S)-6-Ethoxymethoxy-4-(phenylsulfonyl)bicyclo[3.3.0]oct-1-en-3-one(307002-99-9)

Safety Data

• Hazardous Substances Data: 307002-99-9(Hazardous Substances Data)

Upstream product

• 307003-19-6 (S)-(E)-3-Ethoxymethoxy-1-(phenylsulfonyl)hept-1-en-6-yne 
• 307002-95-5 (1E,3S)-1-(Phenylsulfonyl)hept-1-en-6-yn-3-ol 

Relevant articles and documents

endo-selective intramolecular Pauson - Khand reactions of γ-oxygenated-αβ-unsaturated phenylsulfones

A wide variety of 1,6-enynes and 1,7-enynes incorporating γ-oxygenated-α,β-unsaturated phenylsulfone moieties have readily been prepared by piperidine-promoted condensation of the corresponding alkynyl aldehyde with phenylsulfonyl-(p-tolylsulfinyl)methane and further protection of the hydroxyl group. Despite the enduring claim concerning the unsuitability of electronically deficient olefins in Pauson - Khand reactions, we report that these 1-sulfonylated enynes are excellent substrates in intramolecular Pauson - Khand reactions under both thermal and amine N-oxide-promoted conditions. Moreover, in contrast with the usual exo-selective Pauson - Khand cyclization of allylic substituted enynes, the reactions of these 1-sulfonylated-3-oxygenated enynes occur with a moderate or high endo selectivity. The evaluation of the chemical and stereochemical scope of the process in comparison with the Pauson - Khand cyclization of non-sulfonylated enynes, its application to the stereo-selective preparation of optically pure C6-substituted bicyclo[3.3.0]oct-1-en-3-ones, and the interpretation of the stereochemical outcome are also discussed.