Journal of the American Chemical Society
Communication
(15) Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. J. Am.
Chem. Soc. 2010, 132, 2136.
(16) Trost, B. M. Science 1991, 254, 1471.
Program of Global Experts, the Fundamental Research Funds
for Central Universities, and the Cross-disciplinary Collabo-
rative Teams Program for Science, Technology and Innovation
(2014-2016) from the Chinese Academy of Sciences. We thank
Dr. C. E. Stivala (Stanford University) for his assistance with
the manuscript preparation.
(17) For some reviews: (a) Godula, K.; Sames, D. Science 2006, 312,
67. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107,
174. (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(d) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(e) McMurray, L.; O’Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40,
1885. (f) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int.
Ed. 2012, 51, 8960. (g) Wencel-Delord, J.; Glorius, F. Nat. Chem.
2013, 5, 369.
REFERENCES
■
(1) Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl.
1966, 5, 385.
(18) (a) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am.
Chem. Soc. 2004, 126, 9186. (b) Lafrance, M.; Fagnou, K. J. Am. Chem.
Soc. 2006, 128, 16496. (c) Lafrance, M.; Rowley, C. N.; Woo, T. K.;
Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754. (d) Campeau, L.-C.;
Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
(19) For a review: Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu,
J.-Q. Chem. Soc. Rev. 2009, 38, 3242. For some typical results: (a) Shi,
B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008,
47, 4882. (b) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-
Q. J. Am. Chem. Soc. 2010, 132, 460. (c) Wasa, M.; Engle, K. M.; Lin,
D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598.
(d) Musaev, D. G.; Kaledinm, A. L.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem.
Soc. 2012, 134, 1690. (e) Chen, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang,
J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc.
2013, 135, 1236. (f) Chu, L.; Wang, X.-C.; Morre, C. E.; Rheingold, A.
L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344. (g) Saget, T.;
Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238.
(h) Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem.
Eur. J. 2012, 18, 4480. (i) Albicher, M. R.; Cramer, N. Angew. Chem.,
Int. Ed. 2009, 48, 9139. (j) Saget, T.; Cramer, N. Angew. Chem., Int. Ed.
(2) (a) Chiral Ferrocenes in Asymmetric Catalysis; Dai, L.-X., Hou, X.-
L., Eds.; Wiley-VCH: Weinheim, Germany, 2010. (b) Hayashi, T.;
Kumada, M. Acc. Chem. Res. 1982, 15, 395. (c) Halterman, R. L. Chem.
Rev. 1992, 92, 965. (d) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35,
1475. (e) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9,
2377. (f) Fu, G. C. Acc. Chem. Res. 2000, 33, 412. (g) Dai, L.-X.; Tu,
T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659.
(h) Colacot, T. J. Chem. Rev. 2003, 103, 3101. (i) Fu, G. C. Acc. Chem.
́
Res. 2004, 37, 542. (j) Arrayas, R. G.; Adrio, J.; Carretero, J. C. Angew.
Chem., Int. Ed. 2006, 45, 7674. (k) Fu, G. C. Acc. Chem. Res. 2006, 39,
853. (l) Arae, S.; Ogasawara, M. J. Synth. Org. Chem. Jpn. 2012, 70,
593.
(3) (a) Barlow, S.; O’Hare, D. Chem. Rev. 1997, 97, 637. (b) de
Azevedo, C. G.; Vollhardt, K. P. C. Synlett 2002, 1019. (c) Ferrocenes;
Hayashi, T., Togni, A., Eds.; VCH: Weinheim, Germany, 1995.
(d) Metallocenes; Togni, A., Haltermann, R. L., Eds.; VCH: Weinheim,
̌
Germany, 1998. (e) Ferrocenes; Step
U.K., 2008.
̌
nicka, P., Ed.; Wiley: Chichester,
(4) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J.
2013, 52, 7865. (k) Nakanishi, M.; Katayev, D.; Besnard, C.; Kundig,
Am. Chem. Soc. 1970, 92, 5389.
(5) (a) Rebiere, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem.,
̀
̈
E. P. Angew. Chem., Int. Ed. 2011, 50, 7438. (l) Anas, S.; Cordi, A.;
Kagan, H. B. Chem. Commun. 2011, 47, 11483. (m) Shintani, R.;
Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305.
(20) Other monodentate ligands, such as PPh3, (R)-MONOPHOS
are inactive for this transformation.
Int. Ed. Engl. 1993, 32, 568. (b) Riant, O.; Samuel, O.; Kagan, H. B. J.
Am. Chem. Soc. 1993, 115, 5835. (c) Richards, C. J.; Damalidis, T.;
Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. (d) Sammakia, T.;
Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10.
(e) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (f) Metallinos, C.;
Snieckus, V. Org. Lett. 2002, 4, 1935.
(21) The corresponding reaction with aryl bromide gave an 81%
yield of 5a with 99% ee.
(22) A possible mechanism proposed by Maseras, Echavarren, and
Fagnou et al. that the carbonate or carboxylates act as intramolecular
proton abstraction species for a concerted depronation/metalation
process. García-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren,
A. M. J. Am. Chem. Soc. 2006, 128, 1066. Also see ref 18d.
(6) For the resolution of planar chiral molecules, see: (a) Alba, A.-N.
R.; Rios, R. Molecules 2009, 14, 4747. (b) Thomson, J. B. Tetrahedron
Lett. 1959, 1, 26. (c) Ogasawara, M.; Wu, W.-Y.; Arae, S.; Watanabe,
S.; Morita, T.; Takahashi, T.; Kamikawa, K. Angew. Chem., Int. Ed.
2012, 51, 2951.
(7) (a) Tsukazaki, M.; Tinke, M.; Roglans, A.; Chapell, B. J.; Taylor,
N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685. (b) Laufer, R. S.;
Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629.
(8) Price, D. A.; Simpkins, N. S.; MacLeod, A. M.; Watt, A. P. J. Org.
Chem. 1994, 59, 1961.
(9) (a) Uemura, M.; Nishimura, H.; Hayashi, T. Tetrahedron Lett.
1993, 34, 107. (b) Kamikawa, K.; Harada, K.; Uemura, M.
Tetrahedron: Asymmetry 2005, 16, 1419.
(10) (a) Gotov, B.; Schmalz, H.-G. Org. Lett. 2001, 3, 1753.
(b) Bottcher, A.; Schmalz, H.-G. Synlett 2003, 1595.
̈
(11) (a) Mercier, A.; Yeo, W. C.; Chou, J.; Chaudhuri, P. D.;
Bernardinelli, G.; Kundig, E. P. Chem. Commun. 2009, 5227.
̈
(b) Mercier, A.; Urbaneja, X.; Yeo, W. C.; Chaudhuri, P. D.;
Cumming, G. R.; House, D.; Bernardinelli, G.; Kundig, E. P. Chem.
̈
Eur. J. 2010, 16, 6285. (c) Urbaneja, X.; Mercier, A.; Besnard, C.;
Kundig, E. P. Chem. Commun. 2011, 47, 3739.
̈
(12) Bergin, E.; Hughes, D. L.; Richards, C. J. Tetrahedron:
Asymmetry 2010, 21, 1619.
(13) (a) Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am.
Chem. Soc. 2013, 135, 86. (b) Shi, Y.-C.; Yang, R.-F.; Gao, D.-W.; You,
S.-L. Beilstein J. Org. Chem. 2013, 9, 1891.
(14) Murai, M.; Uenishi, J.; Uemura, M. Org. Lett. 2010, 12, 4788.
For another desymmetrization protocol, see: Kundig, E. P.;
̈
Lomberqet, T.; Braqq, R.; Poulard, C.; Bernardinelli, G. Chem.
Commun. 2004, 1548.
4475
dx.doi.org/10.1021/ja500699x | J. Am. Chem. Soc. 2014, 136, 4472−4475