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ChemComm
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DOI: 10.1039/C5CC09918H
COMMUNICATION
Journal Name
of the abovementioned investigations, a possible mechanism
was proposed and outlined in Scheme 3. The zwitterionic
intermediate Ia or enolate Ib was formed in situ from the
D. Zhang, W. –H. Hu, Angew. Chem. Int. Ed. 2014, 53,
13098.
7
8
D.-F. Chen, F. Zhao, Y. Hu, L.-Z. Gong, Angew. Chem. Int.
Ed. 2014, 53, 10763.
iridium catalyzed diazo decomposition of
1 and 2. For the
iminium catalysis, the additive acid accelerates the formation
a) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta, 2006,
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of an iminium ion II, which effectively trap the zwitterionic
intermediate
hydrolysis of III yields the three-component coupling product
and regenerates chiral amine 4a
I
to afford an enamine III
.
Acid promoted
5
9
a) S. Bertelsen, M. Marigo, S. Brandes, P. Diner, K. A.
Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973.; b) Y.
.
In conclusion, an iridium complex/chiral amine co-
catalyzed three-component reaction of diazoacetates, indoles
Deng, S. Kumar, H. Wang, Chem. Commun., 2014, 50,
4272.
and enals was successfully developed to give functionalized 10 a) Ibrahem, S. Santoro, F. Himo and A. Córdova, Adv.
indole derivatives in good yields and with
a
moderate
Synth. Catal., 2011, 353, 245; b) I. Ibrahem, P. Breistein, A.
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diastereoselectivity and excellent enantioselectivity (up to 98%
ee). The novel iridium and iminium co-catalysis promoted
enals to successfully trap the active zwitterionic intermediate
in a regiospecific 1,4-addition fashion. The matched reactivity
of intermediates I and II and the comparable catalytic rate of
the two catalytic cycles are believed to be critical for the
success of the current trapping process.
L. Bui, J. Dufour, M. Rueping, ACS Catal. 2014, 4, 1021.
11 H. Jiang, D. C. Cruz, Y. Li, V. H. Lauridsen, K. A. Jørgensen,
We greatly thank NSFC (21125209 and 21332003), the
J. Am. Chem. Soc. 2013, 135, 5200.
MOST (2011CB808600), STCSM (15ZR1411000) and Stake Key 12 a) S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira,
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