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Synfacts 2011(7): 0750-0750  
DOI: 10.1055/s-0030-1260648
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective 1,3-Rearrangement of Allenylcarboxylates

Contributor(s): Mark Lautens, Jane Panteleev
X. Zhang, C. Fu, S. Ma*
Zhejiang University, Hangzhou, P. R. of China
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Publikationsdatum:
17. Juni 2011 (online)

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Significance

The authors describe a 1,3-rearrangement of 2,3-allenylcarboxylates 1 to afford 3,4-disubstituted butadienylcarboxylates 2 under rhodium catalysis. This work is quite similar to a gold-catalyzed rearrangement reported by Gagosz and co-workers (Org. Lett. 2007, 9, 985), but the stereoselectivity for the E-alkene is considerably better.