226255-51-2

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 65-85-0 benzoic acid 
• 164021-78-7 (1S,2R)-3-(2-bromoethyl)cyclohex-5-ene-1,2-diol 

Downstream Products

• 200638-14-8 3-<2-<(5S,6S)-5,6-Di(benzoyloxy)cyclohex-1-enyl>ethyl>-<1,3>oxazolidine-2,4-dione 
• 200638-12-6 C₂₅H₂₅NO₇ 
• 255861-19-9 (7S,8S,10bS)-7-(2-Bromo-6-methoxyphenoxy)-8-[tert-butyl(dimethyl)silyloxy]-5,6,7,8,9,10-hexahydro-1H-oxazolo[4,3-a]isoquinolin-3-one 
• 249642-32-8 C₂₅H₂₃NO₆ 

Relevant academic research and scientific papers

Intramolecular N-acyliminium ion-olefin cyclization in the synthesis of optically pure isoquinoline derivatives: Control of stereochemistry and application to synthesis of morphine alkaloids

The 3-[2-(cyclohex-1-enyl)ethyl]-[1,3]oxazoline-2,4-dione derivatives 9, 14 and 16 were subjected to hydride reduction followed by acid-catalyzed olefin-N-acyliminium ion cyclization to afford a series of perhydroisoquinolines 10, 11a, 11b, 19a-19c, 20a, 20b and 21. A mechanism was proposed that accounts for the observed stereoselectivity of the cyclization reactions based on the neighboring group participation by a benzoate group.

Model study for a general approach to morphine and noroxymorphone via a rare heck cyclization

matrix presented ss-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.