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Synfacts 2011(3): 0297-0297  
DOI: 10.1055/s-0030-1259482
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Synthesis of Functionalized Morpholines

Contributor(s): Mark Lautens, Jane Panteleev
M. Bandini*, M. Monari, A. Romaniello, M. Tragni
Università di Bologna, Italy
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

A gold-promoted diastereo- and enantioselective synthesis of substituted mor­pholines is described. This work is conceptually similar to recent examples of diastereoselective gold-promoted and enantioselective ruthenium-­catalyzed syntheses of cyclic ethers (A. Aponick, C.-Y. Li, B. Biannic Org. Lett. 2008, 10, 669; S. Tanaka, T. Seki, M. Kitamura Angew. Chem. Int. Ed. 2009, 48, 8948). The use of unactivated allylic alcohols as electrophiles and the application of this strategy to the synthesis of oxazepanyl core are noteworthy.