10.1002/anie.202108534
Angewandte Chemie International Edition
COMMUNICATION
[9]
a) M. Suginome, A. Yamamoto, M. Murakami, J. Am. Chem. Soc. 2003,
125, 6358-6359; b) A. Yamamoto, M. Suginome, J. Am. Chem. Soc.
2005, 127, 15706-15707; c) M. Daini, A. Yamamoto, M. Suginome, J. Am.
Chem. Soc. 2008, 130, 2918-2919.
[28] A. Husain, S. A. Khan, F. Iram, M. A. Iqbal, M. Asif, Eur. J. Med. Chem.
2019, 171, 66-92.
[29] R. Takahashi, K. Kubota, H. Ito, Chem. Commun. 2020, 56, 407-410.
[30] We have determined that O-boron enolates (e.g., derived from a ketone
rather than an ester) do not react under our currently optimized reaction
conditions. See Supporting Information for experimental details.
[10] a) M. Suginome, A. Yamamoto, M. Murakami, Angew. Chem. Int. Ed.
2005, 44, 2380-2382; Angew. Chem. 2005, 117, 2432-2434; b) M.
Suginome, M. Shirakura, A. Yamamoto, J. Am. Chem. Soc. 2006, 128,
14438-14439; c) M. Daini, M. Suginome, Chem. Commun. 2008, 5224-
5226.
[11] For select examples, see: a) R. Alfaro, A. Parra, J. Aleman, J. L. Garcia
Ruano, M. Tortosa, J. Am. Chem. Soc. 2012, 134, 15165-15168; b) H.
Yoshida, I. Kageyuki, K. Takaki, Org. Lett. 2013, 15, 952-955; c) Y. Zhou,
W. You, K. B. Smith, M. K. Brown, Angew. Chem. Int. Ed. 2014, 53, 3475-
3479; Angew. Chem. 2014, 126, 3543-3547; d) H.-Y. Bin, X. Wei, J. Zi,
Y.-J. Zuo, T.-C. Wang, C.-M. Zhong, ACS Catal. 2015, 5, 6670-6679; e)
T. Itoh, Y. Shimizu, M. Kanai, J. Am. Chem. Soc. 2016, 138, 7528-7531;
f) W. Su, T.-J. Gong, Q. Zhang, Q. Zhang, B. Xiao, Y. Fu, ACS Catal.
2016, 6, 6417-6421; g) J. Zhao, K. J. Szabo, Angew. Chem. Int. Ed. 2016,
55, 1502-1506; Angew. Chem. 2016, 128, 1524-1528; h) A. Boreux, K.
Indukuri, F. Gagosz, O. Riant, ACS Catal. 2017, 7, 8200-8204; i) T.
Fujihara, A. Sawada, T. Yamaguchi, Y. Tani, J. Terao, Y. Tsuji, Angew.
Chem. Int. Ed. 2017, 56, 1539-1543; Angew. Chem. 2017, 129, 1561-
1565; j) J. Mateos, E. Rivera-Chao, M. Fananas-Mastral, ACS Catal.
2017, 7, 5340-5344; k) B. Mun, S. Kim, H. Yoon, K. H. Kim, Y. Lee, J.
Org. Chem. 2017, 82, 6349-6357; l) E. Rivera-Chao, M. Fananas-Mastral,
Angew. Chem. Int. Ed. 2018, 57, 9945-9949; Angew. Chem. 2018, 130,
10093-10097; m) E. Rivera-Chao, M. Mitxelena, J. A. Varela, M.
Fañanás-Mastral, Angew. Chem. Int. Ed. 2019, 58, 18230-18234; Angew.
Chem. 2019, 131, 18398-18402; n) Z. Li, L. Zhang, M. Nishiura, G. Luo,
Y. Luo, Z. Hou, ACS Catal. 2020, 10, 11685-11692; o) J. d. Pozo, S.
Zhang, F. Romiti, S. Xu, R. P. Conger, A. H. Hoveyda, J. Am. Chem. Soc.
2020, 142, 18200-18212.
[12] a) S. Xu, Y. Zhang, B. Li, S.-Y. Liu, J. Am. Chem. Soc. 2016, 138, 14566-
14569; b) Y. Zhang, B. Li, S.-Y. Liu, Angew. Chem. Int. Ed. 2020, 59,
15928-15932; Angew. Chem. 2020, 132, 16062-16066.
[13] Y. Yang, J. Jiang, H. Yu, J. Shi, Chem. Eur. J. 2018, 24, 178-186.
[14] a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422; b) B.
M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2944.
[15] M. Braun, Modern Enolate Chemistry: From Preparation to Applications
in Asymmetric Synthesis, John Wiley & Sons, 2015.
[16] Z. He, A. Zajdlik, A. K. Yudin, Dalton Trans. 2014, 43, 11434-11451.
[17] A. Abiko, T. Inoue, S. Masamune, J. Am. Chem. Soc. 2002, 124, 10759-
10764.
[18] N. J. Bell, A. J. Cox, N. R. Cameron, J. S. O. Evans, T. B. Marder, M. A.
Duin, C. J. Elsevier, X. Baucherel, A. A. D. Tulloch, R. P. Tooze, Chem.
Commun. 2004, 1854-1855.
[19] E. W. H. Ng, K.-H. Low, P. Chiu, J. Am. Chem. Soc. 2018, 140, 3537-
3541.
[20] a) J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10,
6615-6620; b) A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem.
B 2009, 113, 6378-6396.
[21] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji,
X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts,
B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L.
Sonnenberg, Williams, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng,
A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N.
Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J.
Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T.
Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M.
J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T.
A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J.
C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C.
Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O.
Farkas, J. B. Foresman, D. J. Fox, Gaussian 09, Revision D.01;
Gaussian Inc.: Wallingford, CT, 2009.
[22] D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 6338-6361;
Angew. Chem. 2008, 120, 6438-6461.
[23] S. Xu, F. Haeffner, B. Li, L. N. Zakharov, S.-Y. Liu, Angew. Chem. Int.
Ed. 2014, 53, 6795-6799; Angew. Chem. 2014, 126, 6913-6917.
[24] At elevated temperatures, C-boron enolate 2 begins to decompose to
dimethyl ketene and methoxycatecholborane.
[25] Deposition Numbers 2091128 and 2091129 (for compound
2 and
compound 8e, respectively) contain the supplementary crystallographic
data for this paper. These data are provided free of charge by the joint
Cambridge Crystallographic Data Centre and Fachinforma- tionszentrum
[26] a) H. Mori, K. Ikoma, Y. Masui, S. Isoe, K. Kitaura, S. Katsumura,
Tetrahedron Lett. 1996, 37, 7771-7774; b) H. Mori, K. Ikoma, S. Isoe, K.
Kitaura, S. Katsumura, J. Org. Chem. 1998, 63, 8704-8718; c) H. Mori,
S. Katsumura, J. Syn. Org. Chem. Jpn. 2003, 61, 857-867.
[27] a) Y. Miyazawa, T. Ohashi, K. Kawaguchi, N. Tanaka, R. Katsuta, A.
Yajima, T. Nukada, K. Ishigami, Flavour Fragr. J. 2020, 35, 341-349; b)
R. G. Berger, Flavours and fragrances: chemistry, bioprocessing and
sustainability, Springer Science & Business Media, 2007.
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