COMMUNICATIONS
Asymmetric Bromine–Lithium Exchange: Application
solved in 10 mL of dry toluene was added to the medium.
The reaction was carried out during 2 h at À788C. Then it
was quenched with 4 or 5 equiv. of the appropriate electro-
phile at À788C, and finally allowed to reach room tempera-
ture during 2 h. Then it was quenched with water and fol-
lowed by an extraction with EtOAc. The combined organic
fractions were dried over sodium sulfate, filtered and con-
centrated under reduced pressure followed by silica gel flash
chromatography or crystallization.
[4] a) T. Saito, N. Sayo, Z. Xiaoyaong, T. Yokozawa, (Taka-
sago International Corporation), European Patent EP
0850945, 1998; b) T. Saito, T. Yokozawa, T. Ishizaki, T.
Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth.
Catal. 2001, 343, 264–267.
[5] a) S. Duprat de Paule, N. Champion, V. Vidal, J.-P.
GenÞt, P. Dellis, (SYNKEM), French Patent FR
2,830,254, 2001; b) S. Duprat de Paule, N. Champion, V.
Vidal, J.-P. GenÞt, P. Dellis, (SYNKEM), WO Patent
WO 03029259, 2003.
[
6] S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-
Vidal, J.-P. GenÞt, N. Champion, P. Dellis, Angew.
Chem. 2004, 116, 324–329; Angew. Chem. Int. Ed. 2004,
Acknowledgements
43, 320–325.
[
7] a) R. Schmid, E. A. Broger, M. Cereghetti, Y. Crameri,
J. Foricher, M. Lalonde, R. K. Müller, M. Scalone, G.
Schoettel, U. Zutter, Pure Appl. Chem. 1996, 68, 131–
The authors thank the Swiss National Research Foundation
(Grant No. 200020-126663) and COST action CM0905 (SER
Contract No. C11.0108) for financial support.
138; b) F. R. Leroux, H. Mettler, Adv. Synth. Catal.
2
007, 349, 323–336; c) L. Qiu, J. Wu, S. Chan, T. T.-L.
Yeung, J.-X. Ji, R. Guo, C.-C. Pai, Z. Zhou, X. Li, Q.-
References
H. Fan, A. S. C. Chan, Proc. Natl. Acad. Sci. USA 2004,
101, 5815–5820; d) L. Qiu, F. Y. Kwong, J. Wu, W. H.
[
1] a) A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T.
Lam, S. Chan, W.-Y. Yu, Y.-M. Li, R. Guo, Z. Zhou,
A. S. C. Chan, J. Am. Chem. Soc. 2006, 128, 5955–5965;
e) S. Wang, J. Li, T. Miao, W. Wu, Q. Li, Y. Zhuang, Z.
Zhou, L. Qiu, Org. Lett. 2012, 14, 1966–1969; f) W. Wu,
S. Wang, Y. Zhou, Y. He, Y. Zhuang, L. Li, P. Wan, L.
Wang, Z. Zhou, L. Qui, Adv. Synth. Catal. 2012, 354,
2395–2402.
Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102,
7932–7934; b) K. Tani, T. Yamagata, S. Otsuka, S. Aku-
tagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A.
Miyashita, R. Noyori, J. Chem. Soc. Chem. Commun.
1
982, 600–601; c) K. Tani, T. Yamagata, S. Akutagawa,
H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashi-
ta, R. Noyori, S. Otsuka, J. Am. Chem. Soc. 1984, 106,
[8] a) Q. Perron, J. Praz, A. Alexakis, Tetrahedron: Asym-
metry 2009, 20, 1004–1007; b) Q. Perron, A. Alexakis,
Adv. Synth. Catal. 2010, 352, 2611–2620; c) J. Graff, T.
Debande, J. Praz, L. GuØnØe, A. Alexakis, Org. Lett.
2013, 15, 4270–4273.
5208–5217; d) K. Tani, T. Yamagata, Y. Tatsuno, Y. Ya-
magata, K. Tomita, S. Akutagawa, H. Kumobayashi, S.
Otsuka, Angew. Chem. 1985, 97, 232–234; Angew.
Chem. Int. Ed. Engl. 1985, 24, 217–219.
[
2] a) H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S.
Akutagawa, S. Inoue, I. Kasahara, R. Noyori, J. Am.
Chem. Soc. 1987, 109, 1596–1597; b) T. Ohta, H.
Takaya, M. Kitamura, K. Nagai, R. Noyori, J. Org.
Chem. 1987, 52, 3174–3176; c) R. Noyori, T. Ohkuma,
M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S.
Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856–5858.
3] a) R. Schmid, M. Cereghetti, B. Heiser, P. Schçnholzer,
H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897–929;
b) R. Schmid, J. Foricher, M. Cereghetti, P. Schçnholz-
er, Helv. Chim. Acta 1991, 74, 370–388; c) M. Cereghet-
ti, A. Rageot, European Patent EP 0511558A2, 1992;
d) E. A. Broger, J. Foricher, B. Heiser, R. Schmid, U.S.
Patent 5,274,125, 1993; e) E. A. Broger, M. Cereghetti,
PCT WO 93/15089, 1993; f) J. Foricher, B. Heiser, R.
Schmid, U.S. Patent 5,302,738, 1994; g) M. Cereghetti,
W. Arnold, E. A. Broger, A. Rageot, Tetrahedron Lett.
[9] L. Bonnafoux, R. Scoppelliti, F. R. Leroux, F. Colobert,
Tetrahedron Lett. 2007, 48, 8768–8772.
[10] M. Cereghetti, W. Arnold, E. A. Boger, A. Rageot, Tet-
rahedron Lett. 1996, 37, 5347–5350.
[11] L. Bonnafoux, R. Gramage-Doria, F. Colobert, F. R.
Leroux, Chem. Eur. J. 2011, 17, 11008–11016.
[12] J. Praz, L. GuØnØe, S. Aziz, A. Berkessel, A. Alexakis,
Adv. Synth. Catal. 2012, 354, 1780–1790.
[
[13] Z. Zhang, H. Qian, J. Longmire, X. Zhang, J. Org.
Chem. 2000, 65, 6223–6226.
[14] A. J. Deeming, D. M. Speel, M. Stchedroff, Organome-
tallics 1997, 16, 6004–6009.
[15] CCDC 1056990, CCDC 1056991, CCDC 1056992,
CCDC 1056993, CCDC 1056994, CCDC 1056995,
CCDC 1056996, CCDC 1056997, CCDC 1056998,
CCDC 1056999, and CCDC 1057000, contain the sup-
plementary crystallographic data for this paper (L1, L2,
L4 to L12, respectively). These data can be obtained
1
996, 37, 5343–5346; h) M. Cereghetti, W. Arnold,
E. A. Broger, A. Rageot, Tetrahedron Lett. 1996, 37,
347–5350.
5
Adv. Synth. Catal. 2015, 357, 2833 – 2839
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