Probing the stereoselectivity of the Heck arylation of endocyclic enecarbamates with diazonium salts. Concise syntheses of (2S,5R)-phenylproline methyl ester and Schramm's C-azanucleoside.
[reaction: see text] The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.
Severino
Elias A
EA
Instituto de Química, Universidade Estadual de Campinas, C P 6154, 13084-971, Campinas, SP, Brazil.
Costenaro
Edson R
ER
Garcia
Ariel L L
AL
Correia
Carlos Roque D
CR
D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002766:Cholecystokinin / Q000037:antagonists & inhibitors; D003979:Diazonium Compounds / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000981:Antiprotozoal Agents; D002219:Carbamates; D003979:Diazonium Compounds; D004952:Esters; D009705:Nucleosides; C473422:phenylproline methyl ester; D002766:Cholecystokinin; D011392:Proline