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(a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178. (c) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539-1542.
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Yamada, Y.M.A.1
Yoshikawa, N.2
Sasai, H.3
Shibasaki, M.4
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2
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0033526380
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(a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178. (c) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539-1542.
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Yoshikawa, N.1
Yamada, Y.M.A.2
Das, J.3
Sasai, H.4
Shibasaki, M.5
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3
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0000148255
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(a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178. (c) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539-1542.
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Org. Lett.
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Kumagai, N.1
Matsunaga, S.2
Yoshikawa, N.3
Ohshima, T.4
Shibasaki, M.5
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5
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0035833675
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Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497-2500.
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Trost, B.M.1
Silcoff, E.R.2
Ito, H.3
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6
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0037160423
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Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
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Evans, D.A.1
Tedrow, J.S.2
Shaw, J.T.3
Downey, C.W.4
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7
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0037018454
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Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127-1130.
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Evans, D.A.1
Downey, C.W.2
Shaw, J.T.3
Tedrow, J.S.4
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8
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0001625277
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Under our conditions N-acyloxazolidinones were unreactive
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For a stoichiometric, Sn(OTt)2/chiral diamine-mediated aldol reaction with theses substrates, see Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1983, 297-300. Under our conditions, N-acyloxazolidinones were unreactive.
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(1983)
Chem. Lett.
, pp. 297-300
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Iwasawa, N.1
Mukaiyama, T.2
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9
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0037905854
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note
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3.
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10
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0037567767
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note
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n. Conversion suffered greatly with <2 equiv of 2.6-lutidine.
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11
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0037073238
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For examples of Ni(II) complexes in chiral Lewis acid catalysis, see: (a) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356.
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Itoh, K.1
Kanemasa, S.2
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12
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0032477318
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For examples of Ni(II) complexes in chiral Lewis acid catalysis, see: (a) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356.
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J. Am. Chem. Soc.
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Kanemasa, S.1
Oderaotoshi, Y.2
Tanaka, J.3
Wada, E.4
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13
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0038243317
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note
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2 thus generated in situ be catalytically active.
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14
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0000070865
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Synthesis: Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
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J. Org. Chem.
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Evans, D.A.1
Peterson, G.S.2
Johnson, J.S.3
Barnes, D.M.4
Campos, K.R.5
Woerpel, K.A.6
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15
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0037567765
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See Supporting Information for X-ray crystallographic data
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See Supporting Information for X-ray crystallographic data.
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16
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0038243316
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note
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The anhydrous catalyst was stored in a glovebox. Hydrated catalyst was less effective in aldol reactions. See Supporting Information for X-ray crystallographic data.
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17
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0037905853
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note
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With the preformed catalyst, conversion increased by 5% and enantioselectivity by 1-2%.
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18
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0037905855
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note
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Suprisingly, enantioselectivity for p-MeOPhCHO was moderate (62%).
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19
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0013217692
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(a) Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1982, 1903-1906. (b) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775-777.
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Mukaiyama, T.1
Iwasawa, N.2
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0034704636
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(a) Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1982, 1903-1906. (b) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775-777.
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Crimmins, M.T.1
Chaudhary, K.2
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21
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0037567766
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note
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For a similar catalytic cycle, see ref 3b.
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22
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0037905856
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note
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Ancillary ligands are omitted for the sake of clarity. The aldol transition state likely involves a five- or six-coordinate nickel complex.
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23
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33947468884
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(a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923. (b) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hasimoto, K.; Fujita, E J. Org. Chem. 1986, 51, 2391-2393. (c) Hsiao, C.-N.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201-2206. See also refs 3b and 14.
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Zimmerman, H.E.1
Traxler, M.D.2
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(a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923. (b) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hasimoto, K.; Fujita, E J. Org. Chem. 1986, 51, 2391-2393. (c) Hsiao, C.-N.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201-2206. See also refs 3b and 14.
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Nagao, Y.1
Hagiwara, Y.2
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Ochiai, M.4
Inoue, T.5
Hasimoto, K.6
Fujita, E.7
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(a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923. (b) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hasimoto, K.; Fujita, E J. Org. Chem. 1986, 51, 2391-2393. (c) Hsiao, C.-N.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201-2206. See also refs 3b and 14.
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Hsiao, C.-N.1
Liu, L.2
Miller, M.J.3
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