Conjugated Addition Of Bis(Oxazolinyl)Zinc To Substituted 2-Nitrovinyl Benzenes: An Alternative Synthesis Of (+/-)-Rolipram

In this letter we present a new 2,4,4-trimethyl-2-oxazoline anion-zinc derivative that has a remarkable thermal stability when compared with the corresponding cyanocuprate counterpart. The yields from conjugated addition to several 2-nitrovinyl benzenes are moderate to good and the reaction itself is easier to execute and cleaner. As an application, this methodology was applied to an alternative synthesis of (+/-)-Rolipram, a drug with several interesting biological activities. (c) 2006 Elsevier Ltd. All rights reserved.