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Synfacts 2015; 11(1): 0080
DOI: 10.1055/s-0034-1379659
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Titanium-Mediated Cycloaddition

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Yoshikai M, Ishibashi R, Yamada Y, Hanamoto T * Saga University, Japan
TiF4-Mediated Regioselective Cycloaddition of 2-(Trifluoromethyl)-N-tosylaziridine to Nitriles.

Org. Lett. 2014;
16: 5509-5511
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

titanium - cycloaddition

Significance

The authors describe a mild and ­efficient [3+2] cycloaddition of 2-(trifluoromethyl)-N-tosylaziridine to various nitriles using TiF4 as a Lewis acid, to give the corresponding 4-(trifluoromethyl)-1,3-imidazolines in good yields and excellent regioselectivity.


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Comment

From a mechanistic point of view, the authors assume that the aziridine is activated by TiF4, which is then attacked by the nitrile to afford the betaine intermediate, which collapses to form the 1,3-imidazole.


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