The Journal of Organic Chemistry
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ASSOCIATED CONTENT
Supporting Information
General experimental procedures, characterizations of the
catalyst, and determination of enantiomeric excess for cyclic
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AUTHOR INFORMATION
Notes
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1623. (b) Berkessel, A.; Brandenburg, M. Org. Lett. 2006, 8, 4401−
4404. (c) Yan, P.; Jing, H.-W. Adv. Synth. Catal. 2009, 351, 1325−
1332. (d) Ren, W.-M.; Wu, G.-P.; Lin, F.; Jiang, J.-Y.; Liu, C.; Luo, Y.;
*
*
Lu, X.-B. Chem. Sci. 2012, 3, 2094−2102.
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Science 1997, 277, 936−938. (b) Jacobsen, E. N. Acc. Chem. Res. 2000,
The authors declare no competing financial interest.
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3, 421−431. (c) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.;
ACKNOWLEDGMENTS
Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen,
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E. N. J. Am. Chem. Soc. 2002, 124, 1307−1315.
(
This work was supported by the National Natural Science
Foundation of China (NSFC) (Grant 21104007), and the
Program for Changjiang Scholars and Innovative Research
Team in University (IRT13008). X.-B.L. gratefully acknowl-
edges the Chang Jiang Scholars Program (T2011056) from the
Ministry of Education of the People’s Republic of China.
13) Chisholm, M. H.; Zhou, Z.-P. J. Am. Chem. Soc. 2004, 126,
1
(
1030−11039.
14) Indeed, in the presence of the metal complex as a catalyst, the
nucleophilic ring opening of propylene oxide preferentially occurs at
the methylene C−O bond rather than the methine C−O bond even at
high temperatures. Thus, the coupling reaction of enantiopure
propylene oxide with CO2 could afford the corresponding five-
membered cyclic product with complete retention of configuration at
the methine carbon. See: (a) Paddock, R. L.; Nguyen, S. T. J. Am.
Chem. Soc. 2001, 123, 11498−11499. (b) Aresta, M.; Dibenedetto, A.;
Gianfrate, L.; Pastore, C. Appl. Catal., A 2003, 255, 5−11. (c) Lu, X.-
B.; Zhang, Y.-J.; Jin, K.; Luo, L.-M.; Wang, H. J. Catal. 2004, 227,
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(
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are efficient for the coupling reaction of CO
selectively afford the corresponding cyclic product at a CO
2
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pressure
2
(
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dx.doi.org/10.1021/jo501926p | J. Org. Chem. XXXX, XXX, XXX−XXX