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Synfacts 2009(9): 1033-1033  
DOI: 10.1055/s-0029-1217783
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

N-Allylic Alkylation of Indoles

Contributor(s): Benjamin List, Frank Lay
H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publikationsdatum:
21. August 2009 (online)

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Significance

Modified cinchona alkaloid hydroquinidine 1,4-phthalazinediyl diether [(DHQD)2PHAL] (1) catalyzes the chemoselective asymmetric N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates. Moderate to excellent yields and enantioselectivities have been achieved and variation in the substitution pattern of electron-rich or electron-deficient indoles was well tolerated. Furthermore, it is shown that the
N-allylic indole products can be converted into pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.