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Synfacts 2011(2): 0165-0165  
DOI: 10.1055/s-0030-1259338
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of 2-Carboxy Cyclic Ethers

Contributor(s): Mark Lautens, Norman Nicolaus
S.-F. Zhu, X.-G. Song, Y. Li, Y. Cai, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publikationsdatum:
19. Januar 2011 (online)

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Significance

The formation of new carbon-­heteroatom bonds using transition-metal-­catalyzed carbene insertion reactions into X-H bonds (X = O, N, S) is a useful synthetic tool. While highly enantioselective variants of intermolecular O-H insertions are known, selective intramolecular versions have not been developed. Herein, the authors present the first highly enantio-selective copper-catalyzed O-H insertion approach used for the preparation of chiral 2-carb­oxy cyclic ethers of type 2.