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Synfacts 2009(9): 1006-1006  
DOI: 10.1055/s-0029-1217664
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Divergent Cyclization towards Cyclopropanes and Oxetanes

Contributor(s): Mark Lautens, Jane Panteleev
Y. Ye, C. Zheng, R. Fan*
Fudan University, Shanghai, P. R. of China
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

The authors report a divergent cyclization of Michael adducts 1 to yield either cyclopropanes 2 or oxetanes 3. The formation of oxetanes is noteworthy since the synthesis of these important synthons (see Book below) can be challenging. The selectivity between the two pathways is achieved through variation of the solvent, and moderate to good yields can be achieved for both products.

Book: B. Alcaide, P. Almendros Four-Membered Ring Systems, In Progress in Heterocyclic Chemistry, Vol. 19; G. Gribble, J. Joule, Eds.; Elsevier Sci Ltd.: UK, 2008, 92-111.