Organic Letters
Letter
Lehmann, C.; Schonholzer, P.; Spiegler, C.; Muller, K. Helv. Chim.
Acta 1995, 78, 703.
̈
̈
Notes
The authors declare no competing financial interest.
(18) (a) For reviews, see: (a) Akiyama, T. Chem. Rev. 2007, 107,
5744. (b) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
(c) Terada, M. Chem. Commun. 2008, 4097. (d) Rueping, M.;
Kuenkel, A.; Atodiresei, I. Chem. Soc. Rev. 2011, 40, 4539. (e) Parmar,
D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047.
ACKNOWLEDGMENTS
■
We gratefully acknowledge a Grant-in-Aid for Scientific
Research (Y.T.) on Innovative Areas “Advanced Molecular
Transformations by Organocatalysis” and a Grant-in-Aid for
Challenging Exploratory Research (Y.K.) from MEXT, Japan.
REFERENCES
(1) (a) Viso, A.; Fernan
Chem. Rev. 2005, 105, 3167. (b) Viso, A.; Fernan
■
́
dez de la Pradilla, R.; García, A.; Flores, A.
dez de la Pradilla, R.;
́
Tortosa, M.; García, A.; Flores, A. Chem. Rev. 2011, 111, PR1.
(2) Okamoto, K.; Sakagami, M.; Feng, F.; Togame, H.; Takemoto,
H.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2012, 77, 1367.
(3) For catalytic asymmetric Mannich reactions using α-substituted
́
oxazolone nucleophiles, see: (a) Avila, E. P.; Justo, R. M. S.;
Goncalves, V. P.; Pereira, A. A.; Diniz, R.; Amarante, G. W. J. Org.
̧
Chem. 2015, 80, 590. (b) Zhang, W.-Q.; Cheng, L.-F.; Yu, J.; Gong, L.-
Z. Angew. Chem., Int. Ed. 2012, 51, 4085. (c) Shi, S.-H.; Huang, F.-P.;
Zhu, P.; Dong, Z.-W.; Hui, X.-P. Org. Lett. 2012, 14, 2010.
(d) Melhado, A. D.; Amarante, G. W.; Wang, Z. J.; Luparia, M.;
Toste, F. D. J. Am. Chem. Soc. 2011, 133, 3517. (e) Liu, X.; Deng, L.;
Jiang, X.; Yan, W.; Liu, C.; Wang, R. Org. Lett. 2010, 12, 876.
(f) Uraguchi, D.; Ueki, Y.; Ooi, T. J. Am. Chem. Soc. 2008, 130, 14088.
(4) Uraguchi, D.; Koshimoto, K.; Ooi, T. Chem. Commun. 2010, 46,
300.
(5) (a) Liang, G.; Tong, M.-C.; Tao, H.; Wang, C.-J. Adv. Synth.
Catal. 2010, 352, 1851. (b) Shang, D.; Liu, Y.; Zhou, X.; Liu, X.; Feng,
X. Chem. - Eur. J. 2009, 15, 3678. (c) Hernan
́ ́
dez-Toribio, J.; Gomez
Arrayas, R.; Carretero, J. C. J. Am. Chem. Soc. 2008, 130, 16150.
́
(d) Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-
D. J. Am. Chem. Soc. 2008, 130, 14362.
(6) For Michael addition/ring-opening reactions with other
nucleophiles, see: (a) Cui, B.-D.; Zuo, J.; Zhao, J.-Q.; Zhou, M.-Q.;
Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2014, 79, 5305.
(b) Geng, Z.-C.; Li, N.; Chen, J.; Huang, X.-F.; Wu, B.; Liu, G.-G.;
Wang, X.-W. Chem. Commun. 2012, 48, 4713.
(7) Bode, J. W.; Fox, R. M.; Baucom, K. D. Angew. Chem., Int. Ed.
2006, 45, 1248.
(8) For competitive oxa-Michael reactions, see: (a) Noel, R.;
̈
̀
Gembus, V.; Levacher, V.; Briere, J.-F. Org. Biomol. Chem. 2014, 12,
1245. (b) Matoba, K.; Kawai, H.; Furukawa, T.; Kusuda, A.; Tokunaga,
E.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010,
49, 5762. (c) Pohjakallio, A.; Pihko, P. M. Chem. - Eur. J. 2009, 15,
́
3960. (d) Ibrahem, I.; Rios, R.; Vesely, J.; Zhao, G.-L.; Cordova, A.
Chem. Commun. 2007, 849. For a competitive 1,2-addition, see:
(e) Vijay Kumar, S.; Saraiah, B.; Misra, N. C.; Ila, H. J. Org. Chem.
2012, 77, 10752.
(9) (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003,
125, 12672. (b) Takemoto, Y. Chem. Pharm. Bull. 2010, 58, 593.
characterization data. CCDC 1442977 (anti-4a) contains the
supplementary crystallographic data for this paper. These data can
be obtained free of charge from the Cambridge Crystallographic Data
(11) Rao, Y. S.; Filler, R. Synthesis 1975, 749.
(12) (a) Blanco-Lomas, M.; Funes-Ardoiz, I.; Campos, P. J.;
Sampedro, D. Eur. J. Org. Chem. 2013, 2013, 6611. (b) Blanco-
Lomas, M.; Campos, P. J.; Sampedro, D. Org. Lett. 2012, 14, 4334.
(13) Robinson, A. J.; Stanislawski, P.; Mulholland, D.; He, L.; Li, H.-
Y. J. Org. Chem. 2001, 66, 4148.
(14) Lohr, T. L.; Marks, T. J. Nat. Chem. 2015, 7, 477.
(15) Pellissier, H. Tetrahedron 2013, 69, 7171.
(16) Ahmed, N.; Babu, B. V. Synth. Commun. 2013, 43, 3044.
(17) (a) Azumaya, I.; Aebi, R.; Kubik, S.; Rebek, J., Jr. Proc. Natl.
Acad. Sci. U. S. A. 1995, 92, 12013. (b) Obrecht, D.; Karajiannis, H.;
D
Org. Lett. XXXX, XXX, XXX−XXX