À
COMMUNICATIONS
Aerobic Oxidation–Olefination–Asymmetric C C Bond Formation
purified by preparative TLC to afford (S)-ethyl 3-phenyl-3-
(p-tolyl)propanoate 4a; yield: 97.1 mg (81%). The ee value
of the product was determined by chiral HPLC analysis
(98% ee).
J. Park, Eur. J. Org. Chem. 2009, 2943; g) H. Lebel, V.
Paquet, J. Am. Chem. Soc. 2004, 126, 11152; h) M.
Davi, H. Lebel, Org. Lett. 2009, 11, 41; i) J. R. Kona,
C. K. King’ondu, A. R. Howell, S. L. Suib, ChemCatCh-
em 2014, 6, 749; j) L. Blackburn, C. X. Pei, R. J. K.
Taylor, Synlett 2002, 215; k) F. R. Pinacho Crisóstomo,
R. Carrillo, T. Martín, F. García-Tellado, V. S. Martín,
J. Org. Chem. 2005, 70, 10099; l) A. R. Bressette, L. C.
Glover IV, Synlett 2004, 738; m) J.-M. Vatle, Tetrahe-
dron Lett. 2006, 47, 715.
Acknowledgements
This work was partially supported by a Grant-in-Aid for Sci-
ence Research from the Japan Society for the Promotion of
Science (JSPS), Global COE Program, The University of
Tokyo, MEXT, Japan, the Japan Science and Technology
Agency (JST), and NEDO. We also thank Mr. Noriaki Kura-
mitsu (The University of Tokyo) for STEM analysis.
[6] a) Ł. Albrecht, H. Jiang, K. A. Jørgensen, Angew.
Chem. 2011, 123, 8642; Angew. Chem. Int. Ed. 2011, 50,
8492; b) D. E. Fogg, E. N. dos Santos, Coord. Chem.
Rev. 2004, 248, 2365; c) F. Gelman, J. Blum, D. Avnir,
J. Am. Chem. Soc. 2000, 122, 11999; d) F. Gelman, J.
Blum, D. Avnir, Angew. Chem. 2001, 113, 3759; Angew.
Chem. Int. Ed. 2001, 40, 3647; e) J.-C. Wasilke, S. J.
Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105,
1001; f) S. Suga, D. Yamada, J. Yoshida, Chem. Lett.
2010, 39, 404.
References
[1] a) O. I. Kolodiazhnyi, Phosphorus Ylides: Chemistry
and Applications in Organic Synthesis, Wiley, Hoboken,
2008; b) B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989,
89, 863; c) S. Matar, L. F. Hatch, Chemistry of Petro-
chemical Processes, Elsevier Science, Amsterdam, 2001.
[2] a) S. Sakuma, M. Sakai, R. Itooka, N. Miyaura, J. Org.
Chem. 2000, 65, 5951; b) F. Xue, D. Wang, X. Li, B.
Wan, Org. Biomol. Chem. 2013, 11, 7893; c) J. F.
Paquin, C. R. J. Stephenson, C. Defieber, E. M. Car-
reira, Org. Lett. 2005, 7, 3821; d) R. Shintani, T. Haya-
shi, Org. Lett. 2011, 13, 350; e) T. Hayashi, Synlett 2001,
879; f) T. Nishikata, S. Kiyomura, Y. Yamamoto, N.
Miyaura, Synlett 2008, 2487; g) L. Navarre, M. Pu-
cheault, S. Darses, J. P. Genet, Tetrahedron Lett. 2005,
46, 4247; h) Y. Takaya, T. Senda, H. Kurushima, M.
Ogasawara, T. Hayashi, Tetrahedron: Asymmetry 1999,
10, 4047.
[7] K. Ding, Y. Uozumi, Handbook of Asymmetric Hetero-
geneous Catalysis, Wiley, Hoboken, 2008.
[8] a) S. Kobayashi, H. Miyamura, Aldrichimica Acta 2013,
46, 3; b) S. Kobayashi, H. Miyamura, Chem. Rec. 2010,
10, 271; c) R. Akiyama, S. Kobayashi, Chem. Rev. 2009,
109, 594; d) H. Miyamura, R. Matsubara, Y. Miyazaki,
S. Kobayashi, Angew. Chem. 2007, 119, 4066; Angew.
Chem. Int. Ed. 2007, 46, 3992; e) H. Miyamura, R. Mat-
subara, S. Kobayashi, Chem. Commun. 2008, 44, 2031.
[9] a) K. Kaizuka, H. Miyamura, S. Kobayashi, J. Am.
Chem. Soc. 2010, 132, 15096; b) C. Lucchesi, T. Inasaki,
H. Miyamura, R. Matsubara, S. Kobayashi, Adv. Synth.
Catal. 2008, 350, 1996.
[10] a) H. Miyamura, H. Min, J.-F. SoulØ, S. Kobayashi,
Angew. Chem. 2015, 127, 7674; Angew. Chem. Int. Ed.
2015, 54, 7564; b) H. Miyamura, T. Yasukawa, S. Ko-
bayashi, Tetrahedron 2014, 70, 6039; c) H. Miyamura, S.
Kobayashi, Acc. Chem. Res. 2014, 47, 1054; d) H. Miya-
mura, G. C. Y. Choo, T. Yasukawa, W.-J. Yoo, S. Ko-
bayashi, Chem. Commun. 2013, 49, 9917; e) H. Miya-
mura, S. Kobayashi, Chem. Lett. 2012, 41, 976; f) H.
Miyamura, M. Morita, T. Inasaki, S. Kobayashi, Bull.
Chem. Soc. Jpn. 2011, 84, 588.
[3] a) S. Afewerki, P. Breistein, K. Pirttila, L. Deiana, P.
Dziedzic, I. Ibrahem, A. Cordova, Chem. Eur. J. 2011,
17, 8784; b) F. Han, J. Chen, X. Zhang, J. Liu, L. Cun,
J. Zhu, J. Deng, J. Liao, Tetrahedron Lett. 2011, 52, 830;
c) J.-Q. Li, X. Quan, P. G. Andersson, Chem. Eur. J.
2012, 18, 10609.
[4] T. Takeda, Modern Carbonyl Olefination: Methods and
Applications, Wiley, Hoboken, 2006.
[11] a) K. Ando, K. Yamada, Tetrahedron Lett. 2010, 51,
3297; b) K. Ando, K. Yamada, Green Chem. 2011, 13,
1143.
[12] a) T. Yasukawa, A. Suzuki, H. Miyamura, K. Nishino,
S. Kobayashi, J. Am. Chem. Soc. 2015, 137, 6616; b) T.
Yasukawa, H. Miyamura, S. Kobayashi, J. Am. Chem.
Soc. 2012, 134, 16963; c) T. Yasukawa, H. Miyamura, S.
Kobayashi, Chem. Sci. 2015, DOI: 10.1039/c5sc02510a.
[5] a) A. Maiti, J. S. Yadav, Synth. Commun. 2001, 31,
1499; b) D. Srimani, G. Leitus, Y. Ben-David, D. Mil-
stein, Angew. Chem. 2014, 126, 11272; Angew. Chem.
Int. Ed. 2014, 53, 11092; c) R. J. K. Taylor, M. Reid, J.
Foot, S. A. Raw, Acc. Chem. Res. 2005, 38, 851; d) G.
Kim, D. G. Lee, S. Chang, Bull. Korean Chem. Soc.
2001, 22, 943; e) F. Alonso, P. Riente, M. Yus, Eur. J.
Org. Chem. 2009, 6034; f) E. Y. Lee, Y. Kim, J. S. Lee,
Adv. Synth. Catal. 2015, 357, 3815 – 3819
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