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Synfacts 2011(11): 1202-1202  
DOI: 10.1055/s-0031-1289188
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Combined C-H Functionalization/Cope Rearrangement with Vinyl Ethers

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Y. Lian, H. M. L. Davies*
Emory University, Atlanta, USA
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Publikationsverlauf

Publikationsdatum:
19. Oktober 2011 (online)

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Significance

In this paper Rh-mediated C-H functionalization/Cope rearrangement (CHCR) involving vinyl ethers is reported, which proceeded in a highly diastereoselective and enantioselective fashion. The CHCR sequence could also be initiated at a primary methyl site of a vinyl ether, which led to the formation of product A with four newly formed contiguous stereocenters (single isomer, 99% ee). The CHCR sequence was efficiently used in the context of kinetic resolution providing a route to enantiopure cyclic vinyl ethers with axial chirality.