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Synfacts 2011(8): 0870-0870  
DOI: 10.1055/s-0030-1260748
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Asymmetric Allylic Alkylation of Indoles and Pyrroles

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Z. Cao, Y. Liu, Z. Liu, X. Feng, M. Zhuang, H. Du*
Beijing National Laboratory of Molecular Sciences, P. R. of China
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

This work expands the Du’s group library of alkene-phosphine hybrid ligands to ­binaphthyl-based species; a number of novel ligands were prepared via a straightforward synthetic sequence. Compound 1 was found as an optimum chiral inductor for Tsuji-Trost-type allylic alkylation of various indoles, which proceeded efficiently (72-99% yield) and with high enantiocontrol (75-94% ee). The paper also demonstrates the first example of Pd-mediated asymmetric allylic alkylation of pyrroles (95-99% yield, 86-98% ee).