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Ohkuma, T.1
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0000155207
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DTBM - SEGPHOS is (4,4′-bi-1,3-benzodioxol) -5,5′- diylbis(di(3,5-di-tert-4-methoxyphenyl)phosphane)
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T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264; DTBM - SEGPHOS is (4,4′-bi-1,3-benzodioxol) -5,5′-diylbis(di(3,5-di-tert-4- methoxyphenyl)phosphane).
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23
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0141631426
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See also: V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 2003, 5, 2417; G. Hughes, M. Kimura, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11253.
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24
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0042693206
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See also: V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 2003, 5, 2417; G. Hughes, M. Kimura, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11253.
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Hughes, G.1
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Buchwald, S.L.3
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25
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4544349151
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note
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Josiphos (1-(2-(diphenylphosphanyl)ferrocenyl)ethyldicyclo- hexylphosphane), Me-DuPHOS (DuPHOS=1,2-bis(2,5-dimethylphospholano)benzene, and BINAP (2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl), all gave ee values that were significantly below those obtained with DTBM-SEGPHOS. DTBM-MeO-BIPHEP (BIPHEP = 6,6′-dimethoybiphenyi-2,2′- diyl(diphenylphosphane)) afforded a comparable ee value, however, the extent of conversion was low in reactions run at -25°C.
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26
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0001486820
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Made following a standard literature method[10c] by using chloro bis(3,5-dimethylphenyl)phosphane; T. V. RajanBabu, T. A. Ayers, G. A. Halliday, K. K. You, J. C. Calabrese, J. Org. Chem. 1997, 62, 6012.
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J. Org. Chem.
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RajanBabu, T.V.1
Ayers, T.A.2
Halliday, G.A.3
You, K.K.4
Calabrese, J.C.5
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27
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4544294425
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note
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The increased concentration was achieved by decreasing the amount of toluene used. 1,1,3,3-tetramethyl disilazane (TMDS; 6 equiv) gave best results.
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-
-
-
28
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4544357570
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note
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See Supporting Information for details.
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-
-
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29
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0011404010
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As reported for BINAP, the (S)-enantiomer of DTBM-SEGPHOS is available by resolution following the protocol for the (R)-enantiomer, but with reliance on the opposite enantiomer of dibenzoyl tartrate; see H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629.
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Takaya, H.1
Mashima, K.2
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Kumobayashi, H.5
Taketomi, T.6
Akutagawa, S.7
Noyori, R.8
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