Journal of the American Chemical Society
COMMUNICATION
Scheme 4. Asymmetric Syntheses of Isoindoline 13 and
Isoindolinone 14
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aryl thiocarbamate and the 6-alkoxy group of the quinoline in the
alkaloid skeleton are tunable, which allowed us to adopt different
substrate skeletons. Further investigation of other applications,
including piperidine formation, and studies of the mechanism are
underway.
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’ ASSOCIATED CONTENT
S
Supporting Information. Experimental procedures, spec-
b
troscopic data, and crystallographic data (CIF). This material is
(7) Catalyst analogues, including carbamate, thiourea, and N-methyl
thiocarbamate, were also examined, and they did not offer any enantio-
selectivity.
’ AUTHOR INFORMATION
Corresponding Author
(8) Details are given in the Supporting Information.
(9) This phenomenon has appeared in some reports. For details, see
refs 3f, 3i, and 4. For a related study, see: Ruasse, M. F.; Argile, A.;
Dubois, J. E. J. Am. Chem. Soc. 1978, 100, 7645–7652.
’ ACKNOWLEDGMENT
(10) Although we were unable to obtain an X-ray structure of
catalyst 8, the crystal structure of 1a shows that the aryl ring and the
thiocarbamate are not coplanar. For the data for 1a, please see ref 3i.
(11) (a) Catino, A. J.; Nichols, J. M.; Forslund, R. E.; Doyle, M. P.
Org. Lett. 2005, 7, 2787–2790. (b) Chen, Z. G.; Wei, J. F.; Wang, M. Z.;
Zhou, L. Y.; Zhang, C. J.; Shi, X. Y. Adv. Synth. Catal. 2009, 351,
2358–2368.
We thank the National University of Singapore (Grant 143-000-
428-112) for financial support. Special thanks to Ms Mei-Chun
Cheng for the cover graphic design.
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