10.1002/anie.201916129
Angewandte Chemie International Edition
COMMUNICATION
Soc. 1998, 120, 2768; l) F. Tanaka, R. A. Lerner, C. F. Barbas, J. Am.
Chem. Soc. 2000, 122, 4835.
[13] a) R. Pluta, N. Kumagai, M. Shibasaki, Angew. Chem. 2019, 131, 2481;
b) X.-J. Li, H.-Y. Xiong, M.-Q. Hua, J. Nie, Y. Zheng, J.-A. Ma,
Tetrahedron 2012, 53, 2117; c) J. Mo, R. Yang, X. Chen, B. Tiwari, Y. R.
Chi, Org. Lett. 2013, 15, 50; d) J. Lin, T. Kang, Q. Liu, L. He, Tetrahedron:
Asymmetry 2014, 25, 949; e) H. Zong, H. Huang, G. Bian, L. Song, J.
Org. Chem. 2014, 79, 23; f) Y. Zheng, H.-Y. Xiong, J. Nie, M.-Q. Hua, J.-
A. Ma, Chem. Commun. 2012, 48, 4308; g) S. Crotti, G. Belletti, N.
DiIorio, E. Marotta, A. Mazzanti, P. Righi, G. Bencivenni, RSC Adv. 2018,
8, 33451
[4]
a) A. Matsuzawa, C. R. Opie, N. Kumagai, M. Shibasaki, Chem. Eur. J.
2014, 20, 68; b) K. Alagiri, S. Lin, N. Kumagai, M. Shibasaki, Org. Lett.
2014, 16, 5301; c) D. Sureshkumar, Y. Kawato, M. Iwata, N. Kumagai,
M. Shibasaki, Org. Lett. 2012, 14, 3108; d) D. A. Evans, D. M. Fitch, T.
E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033; e) S. J.
Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V.
Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C.
A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843.
a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124,
6798; b) A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752;
c) I. K. Mangion, A. B. Northrup, D. W. C. MacMillan, Angew. Chem. Int.
Ed. 2004, 43, 6722; d) R. Ian Storer, David W. C. MacMillan, Tetrahedron
2004, 60, 7705.
[14] For pertinent reviews on the importance of fluorine incorporation, see: a)
D. O’Hagan, Chem. Soc. Rev. 2008, 37, 308I; b) V. Gouverneur, K.
Mꢀller, Fluorine in Pharmaceutical and Medicinal Cemistry, Imperial
College Press, London (UK), 2012; c) K. Mꢀller, C. Faeh, F. Diederich,
Science 2007, 317, 1881; d) S. Purser, P. R. Moore, S. Swallow, V.
Gouverneur, Chem. Soc. Rev. 2008, 37, 320; e) R. Szpera, D. F. J.
Moseley, L. B. Smith , A. J. Sterling, V. Gouverneur, Angew. Chem. Int.
Ed. 2019, 58, 14824; f) D O’Hagan, J. Fluorine Chem. 2010, 131, 1071;
h) Y. Zhu, J. Han, J. Wang, N. Shibata, M. Sodeoka, V. A. Soloshonok,
J. A. S. Coelho, F. D. Toste, Chem. Rev. 2018, 118, 3887; i) J.-P. Begue,
D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine,
Wiley-VCH, Hoboken, 2008; j) Ojima, Fluorine in Medicinal Chemistry
and Chemical Biology, Wiley-Blackwell, Chichester (UK), 2009.
[15] a) W. Yang, Y.-M. Cui, W. Zhou, L. Li, K.-F. Yang, Z.-J. Zheng, Y. Lu, L.-
W. Xu, Synlett 2014, 25, 1461; b) Q. Guo, M. Bhanushali, C.-G. Zhao,
Angew. Chem. Int. Ed. 2010, 49, 9460; c) I. Vlasserou, M. Sfetsa, D.-T.
Gerokonstantis, C. G. Kokotos, P. Moutevelis-Minakakis, Tetrahedron,
2018, 74, 2338; d) N. Duangdee, W. Harnying, G. Rulli, J.-M. Neudorfl,
H. Groger, A. Berkessel, J. Am. Chem. Soc. 2012, 134, 11196; e) N.
Hara, R. Tamura, Y. Funahashi, S. Nakamura, Org. Lett. 2011, 13, 1662;
f) C. G. Kokotos, J. Org. Chem. 2012, 77, 1131; g) L.-H. Qui, Z.-X. Shen,
C.-Q. Shi, Y.-H. Liu, Y.-W. Zhang, Chin. J. Chem. 2005, 23, 584; h) W.
Yang, Y.-M. Cui, W. Zhou, L. Li, K.-Fang Yang, Z.-J. Zheng, Y. Lu, L.-W.
Xu, Synlett 2014, 25, 1461.
[5]
[6]
a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew.
Chem. Int. Ed. Engl. 1997, 36, 1871; Angew. Chem. 1997, 109, 1942; b)
N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am.
Chem. Soc. 1999, 121, 4168; c) M. Shibasaki, N. Yoshikawa, Chem.
Rev. 2002, 102, 2187; d) H. Sasai, T. Suzuki, S. Arai, T. Aria, M.
Yoshikawa, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418.
a) T. Kano, J. Takai, O. Tokuda, K. Maruoka, Angew. Chem. Int. Ed.
2005, 44, 3055; b) T. Kano, H. Sugimoto, K. Maruoka, J. Am. Chem. Soc.
2011, 133, 18130; c) T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J.
Am. Chem. Soc. 2004, 126, 9685; d) T. Ooi, M. Taniguchi, M. Kameda,
K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 4542.
[7]
[8]
a) B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600; b) Corey,
E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287; c) B. M. Trost, H. Ito, J. Am.
Chem. Soc. 2000, 122, 12003; d) T. March, A. Murata, Y. Kobayashi, Y.
Takemoto, Synlett 2017, 28, 1295; e) J. Saadi, H. Wennemers, Nat.
Chem. 2016, 8, 276; f) Shota Sakamoto, Naoya Kazumi, Yusuke
Kobayashi, Chihiro Tsukano, Yoshiji Takemoto, Org. Lett. 2014, 16,
4758; g) H. Torii, M. Nakadai, K. Ishihara, S. Saito and H. Yamamoto,
Angew. Chem. Int. Ed. 2004, 43, 1983; h) Nobuko Ozasaa, Manabu
Wadamotob, Kazuaki Ishiharaa, Hisashi Yamamoto, Synlett 2003, 14,
2219; i) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A.
Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843; j) B. M. Trost, V. S. C.
Yeh, Angew. Chem. Int. Ed., 2002, 41, 861; k) C. Palomo, M. Oiarbide,
A. Laso, Angew. Chem. Int. Ed. 2005, 44, 3881; l) D. A. Evans, D. Seidel,
M. Rueping, H. W. Lam, J. T. Shaw, C. D. Downey, J. Am. Chem. Soc.
2003, 125, 12692; m) H Li, B Wang, L Deng, J. Am. Chem. Soc. 2006,
128, 732.
[16] For previous reports see ref 11 and: a) P. Wang, H.-F. Li, J.-Z. Zhao, Z.-
H. Du, C.-S. Da, Org. Lett. 2017, 19, 2634; for Takemoto’s catalyst, see:
b) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125,
12672.
[17] a) M. G. Nunez, A. J. M. Farley, D. J. Dixon, J. Am. Chem. Soc. 2013,
135, 16348; b) A. M. Goldys, M. G. Nunez, D. J. Dixon, Org. Lett. 2014,
16, 6294; c) A. J. M. Farley, C. Sandford, D. J. Dixon, J. Am. Chem. Soc.
2015, 137, 15992; d) G. P. Robertson, A. J. M. Farley, D. J. Dixon,
Synlett, 2016, 27, 21; e) M. A. Horwitz, B. P. Zavesky, J. I. Martinez-
Alvarado, J. S. Johnson, Org. Lett. 2016, 18, 36; f) M. A. Horwitz, J. L.
Fulton, J. S. Johnson, Org. Lett. 2017, 19, 5783; g) H. Shi, I. M.
Michaelides, B. Darses, P. Jakubec, Q. N. N. Nguyen, R. S. Paton, D. J.
Dixon, J. Am. Chem. Soc. 2017, 139, 17755; h) M. Formica, G. Sorin, A.
J. M. Farley, J. Diaz, R. S. Paton, D. J. Dixon, Chem. Sci. 2018, 9, 6969.
[18] Subjecting enantioenriched product 3a to the optimized reaction
conditions showed no erosion of er after 7 days, suggesting the aldol
products are resistant to the retro-aldol reaction under BIMP catalysis
conditions.
[9]
For reactions with isatins, see: a) Q. Guo, M. Bhanushali, C.-G. Zhao,
Angew. Chem. Int. Ed. 2010, 49, 9460; b) H. Gao, Z. L. Luo, P. J. Ge, J.
Q. He, F. Zhou, P. P. Zheng, J. Jiang, Org. Lett. 2015, 17, 5962; c) G.
Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C.
Tomasini, J. Org. Chem. 2005, 70, 7418; for glyoxal derivatives, see: d)
A. Matsuzawa, H. Noda, N. Kumagai, M. Shibasaki, J. Org. Chem.
2017, 82, 8304; e) Y. Hayashi M. Kojima, ChemCatChem 2013, 5, 2883;
Soc. 2006, 128, 7442; g) J. Yu, X. Zhao, Z. Miao, R. Chen, Org. Biomol.
Chem. 2011, 9, 6721; h) G. B. Vamisetti, R. Chowdhury, S. K. Ghosh,
Org. Biomol. Chem. 2017, 15, 3869; for keto-esters, see: i) A.-J.Wei, J.
[19] The synthesis of aldol products of this type (bearing an additional
stereocentre at the alpha-keto position) is known to be extremely
challenging due to rapid reversibility. For example, see: S. Sasaki, K.
Kikuchi, T. Yamauchi, K. Higashiyama, Synlett 2011, 10, 1431.
[20] N. A. McGrath, M. Brichacek, J. T. Njardarson, J. Chem. Ed. 2010, 87,
1348.
[21] Synthesis and testing of the degradation product (the corresponding
primary amine) confirmed it is catalytically inactive in the aldol reaction
of 1a with 2a.
[10] a) B. List, Tetrahedron 2002, 58, 5573; b) W. Notz, F. Tanaka, C. F.
Barbas, Acc. Chem. Res. 2004, 37, 580; c) P. I. Dalko, L. Moisan, Angew.
Chem. Int. Ed. 2004, 43, 5138.
[11] L. M. Lutete, T. Miyamoto, T. Ikemoto, Tetrahedron. Lett. 2016, 57, 1220.
[12] a) W. S. Matthews, J. E. Bres, J. E. Bartmess, F. G. Bordwell, F. J.
Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum,
N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 7006; b) B. D. Süveges, J.
Podlech, Eur. J. Org. Chem. 2015, 987.
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