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12
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0041904956
-
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note
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STREM Chemicals currently offers research quantities of the DuPhos and BPE ligands and catalysts.
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13
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0001564086
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15
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0035944509
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16
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0001296673
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17
-
-
0042907027
-
-
note
-
Chiral Quest ligand.
-
-
-
-
18
-
-
0041904953
-
-
note
-
Solvias ligand.
-
-
-
-
19
-
-
0041904954
-
-
note
-
Chirotech Ligand.
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20
-
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0030972372
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22
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0042406210
-
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International publication number: WO 99/24444, filed 05/11/1998
-
This concept has been described in the patent literature. See: Berens, H. International publication number: WO 99/24444, filed 05/11/1998.
-
-
-
Berens, H.1
-
23
-
-
0042907025
-
-
note
-
It must also be pointed out that the phosphorous atom is rendered chiral because of the existence of stereogenic carbons in the phospholane ring. Therefore, while the described ligands are P-chirogenic, the stereogenic carbon atoms play the major role in defining the steric environment of the ligands and their corresponding rhodium catalysts.
-
-
-
-
25
-
-
0032564850
-
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Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H. ; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
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Masuda, H.4
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Yamaguchi, K.8
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26
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0037012673
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Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612.
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Tang, W.1
Zhang, X.2
-
27
-
-
0041749668
-
-
A similar P-chirogenic phospholane ligand was reported during the review process of this paper. See: Shimizu, H.; Saito, S.; Kumobayashi, H. Adv. Synth. Catal. 2003, 345, No. 1+2, 185.
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Shimizu, H.1
Saito, S.2
Kumobayashi, H.3
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28
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0028880395
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Imamoto, T.1
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29
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0001260689
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31
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0041904948
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Hammond, P. J.; Lloyd, J. R.; Hall, C. D. Phosphorus Sulfur 1981, 10, 67.
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32
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0041904947
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Beer, P. D.; Hammond, P. J.; Hall, C. D. Phosphorus Sulfur 1981, 10, 185.
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Beer, P.D.1
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Hall, C.D.3
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35
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84987515768
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-
37
-
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0000895308
-
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Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
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39
-
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0000713762
-
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Wadsworth, W. S., Jr.; Larsen, S.; Horten, H. L. J. Org. Chem. 1973, 38, 256.
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Wadsworth W.S., Jr.1
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-
40
-
-
0041904946
-
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Corriu, R.; Lanneau, G.; Leclercq, D. Tetrahedron 1986, 42, 5591.
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Corriu, R.1
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-
41
-
-
0042907023
-
-
note
-
It is noteworthy that the 9:1 ratio of diastereomers 28 and 29 translates to 80% de. That compound 20 is produced in 77% ee is consistent with complete retention of configuration during the displacement of the menthoxy group with MeLi.
-
-
-
-
43
-
-
0031568727
-
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-
44
-
-
0041904949
-
-
note
-
We have also succeeded in synthesizing the racemic chiral diol on 1/2 kilogram scale via this route and then separating the enantiomers via SMB chromatography.
-
-
-
-
45
-
-
0000740766
-
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Murk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
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-
48
-
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0041904943
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Burk, M. J.; Goel, O. P.; Hoekstra, M. S.; Mich, T. F.; Mulhern, T. A.; Ramsden, J. A. PCT Int. Appl., 2001.
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Burk, M.J.1
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Mulhern, T.A.5
Ramsden, J.A.6
-
49
-
-
10744227163
-
-
It has been speculated that substrate 39 can bind with a rhodium complex of Me-DuPhos. See: Burk, M. J.; de Koning, P. D.; Grote, T. M.; Hoekstra, M. S. ; Hoge, G.; Jennings, R. A.; Kissel, W. S.; Le, T. V.; Lennon, I. C.; Mulhern, T. A.; Ramsden, J. A.; Wade, R. A. J. Org. Chem. 2003, 68, 5731.
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Kissel, W.S.7
Le, T.V.8
Lennon, I.C.9
Mulhern, T.A.10
Ramsden, J.A.11
Wade, R.A.12
-
50
-
-
0042907024
-
-
note
-
It should be noted that substrates 39 and 40 are 1:5.7 E/Z mixtures and that the reaction rates and enantiomeric excesses observed at different reaction pressures might be different for each diastereomer. Pure E substrate could not be isolated for these comparisons, but we have observed that pure Z substrate follows the same enantioselectivity trends versus pressure as the 1:5.7 E/Z mixture.
-
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51
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0029885727
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