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Wiley-VCH Verlag, ChemInform, 22(38), 2007

DOI: 10.1002/chin.200722109

Elsevier, Tetrahedron Letters, 8(48), p. 1507-1509

DOI: 10.1016/j.tetlet.2006.12.007

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Conjugated Addition of Bis(oxazolinyl)zinc to Substituted 2-Nitrovinyl Benzenes: An Alternative Synthesis of (.+-.)-Rolipram

Journal article published in 2007 by Alfredo R. M. Oliveira ORCID, Jose A. F. P. Villar, Fabio Simonelli, Rogerio A. Gariani, Celso L. Wosch, Paulo H. G. Zarbin
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.