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Synfacts 2009(9): 1033-1033
DOI: 10.1055/s-0029-1217783
DOI: 10.1055/s-0029-1217783
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New YorkN-Allylic Alkylation of Indoles
H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. August 2009 (online)

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.