Download PDF
Synfacts 2014; 10(2): 0159
DOI: 10.1055/s-0033-1340590
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

[3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Guo H, * Liu H, Zhu F.-L, Na R, Jiang H, Wu Y, Zhang L, Li Z, Yu H, Wang B, Xiao Y, Hu X.-P, * Wang M. China Agricultural University, Beijing and Dalian Institute of Chemical Physics, P. R. of China
Enantioselective Copper-Catalyzed [3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines.

Angew. Chem. Int. Ed. 2013;
52: 12641-12645
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
20 January 2014 (online)

 
 PDF Download Permissions and Reprints

Key words

azomethine ylides - azomethine imines - copper

Significance

With the use of a [3+3] cycloaddition the authors were able to generate biologically active hexahydro-8H-pyrazolo[1,2-a][1,2,4]triazin-8-one derivatives. In a highly diastereo- and enantioselective manner, azomethine ylides were reacted with azomethine imines in the presence of copper and ferrocenyl chiral P,N-ligands.


#

Comment

[3+3] And [3+4] cycloadditions with azomethine ylides are not as well known as their [3+2] counterparts. Pioneering work in the use of 1,3-dipolar [3+2] cycloadditions with azomethine ylides was made by the groups of Jørgensen ( Angew. Chem. Int. Ed. 2002, 41, 4236) and Zhang (J. Am. Chem. Soc. 2002, 124, 13400). In the presence of LiBH4 the product of the [3+3] adduct rearranged to an unexpected compound. This interesting molecule was formed as a single diastereomer, but was found to be racemic.


#
#


   Permissions and Reprints