Zinc, Lithium and Magnesium Carbenoids: Chemical Properties and Relevant Applications in Organic Synthesis

Carbenoids are a class of highly reactive reagents that play an important role in modern organic synthesis. These species are very similar to singlet state carbenes since they have an ambiphilic character and react by a concerted mechanism allowing stereospecific transformations. Herein, we discuss these and other chemical aspects of zinc, lithium and magnesium carbenoids as well as relevant applications of these intermediates in organic synthesis.

Keywords:
carbenoid; organometallic; reactive intermediate; stereospecific synthesis

Authorship

Rodolfo H. V. Nishimura ^**e-mail: gclososki@fcfrp.usp.br

Núcleo de Pesquisa em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café s/n, 14040-903 Ribeirão Preto-SP, BrazilUniversidade de São PauloBrazilRibeirão Preto, SP, BrazilNúcleo de Pesquisa em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café s/n, 14040-903 Ribeirão Preto-SP, Brazil

Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, 14040-901 Ribeirão Preto-SP, BrazilUniversidade de São PauloBrazilRibeirão Preto, SP, BrazilDepartamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, 14040-901 Ribeirão Preto-SP, Brazil

Valter E. Murie ^**e-mail: gclososki@fcfrp.usp.br

Rafael A. Soldi ^**e-mail: gclososki@fcfrp.usp.br

João L. C. Lopes ^**e-mail: gclososki@fcfrp.usp.br

Giuliano C. Clososki ^**e-mail: gclososki@fcfrp.usp.br

*e-mail: gclososki@fcfrp.usp.br

Rodolfo Hideki Vicente Nishimura studied chemistry at Universidade de São Paulo (2007-2012) and received the Master degree in Organic Chemistry under guidance of Giuliano Cesar Clososki (2015). Currently, he is a PhD student at the Universidade de São Paulo in Ribeirão Preto, working in the development of new synthetic methodologies employing organometallic bases in order to obtain bioactive substances.

Valter Eduardo Murie received his degree in Pharmacy and Biochemistry at the Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP) in the Universidade de São Paulo in 2004, with focus in Drugs and Medicines. Currently he is graduate student under guidance of Prof Giuliano C. Clososki. His researchinterests include the development of new synthetic methods and drug synthesis.

Rafael Augusto Soldi graduated in Chemistry (2003) and completed his doctorate degree (2013) at the Universidade Federal do Paraná under the supervision of Prof Paulo H. G. Zarbin. Presently he is a postdoctoral fellow at the Universidade de São Paulo - Ribeirão Preto. His research interests include the development of new synthetic methods and natural product synthesis.

Prof Giuliano Cesar Clososki obtained his BSc and Master degree in Chemistry at the Universidade Federal do Paraná working with Prof Fabio Simonelli. He spent 1 year at the UCSB with Prof Lipshutz and got his PhD degree at the Universidade de São Paulo (2005) under the supervision of Prof João V. Comasseto. After postdoctoral research with Prof José A. R. Rodrigues (Unicamp) and Prof Paul Knochel (LMU) he accepted a position at the Universidade de São Paulo, Ribeirão Preto (2008). His research interests include the development of new synthetic methods using organometallic reagents and natural product synthesis.

Prof João Luis Callegari Lopes obtained a BSc degree in Pharmacy and a PhD in Chemistry at the Universidade de São Paulo. He is retired as a Full Professor of Organic Chemistry at the Departamento de Física e Química, Faculdade de Ciências Farmacêuticas, Ribeirão Preto, Universidade de São Paulo since 2014, but is still developing his activities as a Senior Professor. His research deals with organic chemistry, with emphasis on natural products chemistry and mass spectrometry.

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