Highly Selective Tandem Nitrone Formation/1,3-Dipolar Cycloaddition Catalyzed by Ruthenium Porphyrin

Highly Selective Tandem Nitrone Formation/1,3-Dipolar Cycloaddition Catalyzed by Ruthenium Porphyrin

Reddy, Annapureddy Rajasekar; Guo, Zhen; Siu, Fung-Ming; Lok, Chun-Nam; Liu, Fuli; Yeung, Kai-Chung; Zhou*, Cong-Ying; Che, Chi-Ming

Abstract:

1,3-Dipolar cycloaddition of nitrones with alkenes is a powerful method for the synthesis of isoxazolidines which are frequently present in bioactive molecules and are versatile building blocks used in organic synthesis. Conventional approaches to nitrones usually require the addition of oxidant, acid or the use of harsh reaction conditions and thus have limited substrate scope. In addition, the issue of low diastereo-control is often encountered in 1,3-dipolar cycloaddition reaction of acyclic nitrones. Thus, there has been a continuing interest in developing new methods for selective nitrone formation/1,3-dipolar cycloaddition cascade under mild reaction conditions.

1,3-Dipolar cycloaddition of nitrones with alkenes is a powerful method for the synthesis of isoxazolidines which are frequently present in bioactive molecules and are versatile building blocks used in organic synthesis. Conventional approaches to nitrones usually require the addition of oxidant, acid or the use of harsh reaction conditions and thus have limited substrate scope. In addition, the issue of low diastereo-control is often encountered in 1,3-dipolar cycloaddition reaction of acyclic nitrones. Thus, there has been a continuing interest in developing new methods for selective nitrone formation/1,3-dipolar cycloaddition cascade under mild reaction conditions.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20138270315

Referências bibliográficas

• [1] 1 Kissane, M.; Maguire, A. R. Chem. Soc. Rev., 2010, 39, 845.
• [2] 2 Feuer, H., Ed. Nitrile Oxides, Nitrones And Nitronates in Organic Synthesis Wiley, New Jersey, 2008.

Como citar:

Reddy, Annapureddy Rajasekar; Guo, Zhen; Siu, Fung-Ming; Lok, Chun-Nam; Liu, Fuli; Yeung, Kai-Chung; Zhou*, Cong-Ying; Che, Chi-Ming; "Highly Selective Tandem Nitrone Formation/1,3-Dipolar Cycloaddition Catalyzed by Ruthenium Porphyrin", p-7-7. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20138270315