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Synfacts 2008(8): 0849-0849  
DOI: 10.1055/s-2008-1077910
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Diastereoselective Synthesis of trans-1,2-Diazetidines

Contributor(s): Mark Lautens, Valentina Aureggi
X. Cheng, S. Ma*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

The selective formation of four-membered rings is an important challenge in organic chemistry. The development of an efficient Pd-catalyzed cyclization for the synthesis of trans-1,2-diazetidines from 2,3-allenyl hydrazine and aryl halides is reported. The reaction is highly regio- and diastereoselective and the corresponding products are obtained in good yields. Optically active vinyl 1,2-diazetidines are also efficiently synthesized using the corresponding enantiomerically enriched 2,3-allenyl hydrazines. For previous work, see: S. Ma, F. Yu, J. Li, W. Gao Chem. Eur. J. 2007, 13, 247.