-
4
-
-
0001827606
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Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford
-
For discussions on the coordination chemistry of 2,2́-bipyridines and 1,10-phenanthrolines, see: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 73-98. (b) Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
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Comprehensive Coordination Chemistry
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Reedijk, J.1
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5
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0034299604
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For discussions on the coordination chemistry of 2,2́-bipyridines and 1,10-phenanthrolines, see: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 73-98. (b) Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
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Chem. Rev.
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Kaes, C.1
Katz, A.2
Hosseini, M.W.3
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6
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-
0033936085
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-
For a recent review on chiral bis(oxazolines) in asymmetric transition metal catalyzed reactions, see for example: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
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Acc. Chem. Res.
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Johnson, J.S.1
Evans, D.A.2
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8
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0034615645
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Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377.
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Chem. Commun.
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Rios, R.1
Liang, J.2
Lo, M.M.-C.3
Fu, G.C.4
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10
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-
0000114544
-
-
Supporting Information
-
On heating the acetate 4 with concentrated sulfuric acid for an extended period of time (1 h) the regioselectivity of this elimination reaction was compromised (9:1). Ruble and Fu have reported a related example in which a functionalized pyrindine is formed as a mixture of regioisomers (2:1): Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230 (Supporting Information).
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Ruble, J.C.1
Fu, G.C.2
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11
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4444276636
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For a review on AD reactions, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
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Chem. Rev.
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Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
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12
-
-
1642414117
-
-
note
-
The enantioselectivity of this AD reaction was determined by analytical chiral HPLC (Daicel Chiracel OD column).
-
-
-
-
13
-
-
0343464590
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-
2-symmetric chiral ligand derived from (1R,2R)-trans-1,2- diaminocyclohexane in 80% ee (70% yield). However, the chiral ligand and osmium tetroxide are used stoichiometrically in this reaction; see: Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
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J. Chem. Ed.
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Spivey, A.C.1
Hanson, R.2
Scorah, N.3
Thorpe, S.J.4
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14
-
-
0001532666
-
-
2-symmetric chiral ligand derived from (1R,2R)-trans-1,2- diaminocyclohexane in 80% ee (70% yield). However, the chiral ligand and osmium tetroxide are used stoichiometrically in this reaction; see: Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
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J. Org. Chem.
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Hanessian, S.1
Meffre, P.2
Girard, M.3
Beaudoin, S.4
Sancéau, J.-Y.5
Bennani, Y.6
-
15
-
-
1642391512
-
-
note
-
Interestingly, the overall yield of the corresponding quinoline derivative of the acetal (+)-7 that has been prepared from cyclohexanone by the same procedures was significantly greater. However, the enantiomeric purity of this acetal was poor (∼5% ee).
-
-
-
-
16
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0001213685
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2PHAL using methanesulfonamide as an additive and 1 mol % of potassium osmate dihydrate: (a) Wang, Z.-M.; Kakiuchi, K., Sharpless, K. B. J. Org. Chem. 1994, 59, 6895. (b) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
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J. Org. Chem.
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Wang, Z.-M.1
Kakiuchi, K.2
Sharpless, K.B.3
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17
-
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0000797769
-
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2PHAL using methanesulfonamide as an additive and 1 mol % of potassium osmate dihydrate: (a) Wang, Z.-M.; Kakiuchi, K., Sharpless, K. B. J. Org. Chem. 1994, 59, 6895. (b) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
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Wang, L.1
Sharpless, K.B.2
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20
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0025328473
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(b) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80.
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Bull. Chem. Soc. Jpn.
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Iyoda, M.1
Otsuka, H.2
Sato, K.3
Nisato, N.4
Oda, M.5
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23
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0037603215
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-
For example, see: Malkov, A. V.; Pernazza, D.; Bell, M.; Bella, M.; Massa, A.; Teplý, F.; Meghani, P.; Kočovský, P. J. Org. Chem. 2003, 68, 4727.
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Malkov, A.V.1
Pernazza, D.2
Bell, M.3
Bella, M.4
Massa, A.5
Teplý, F.6
Meghani, P.7
Kočovský, P.8
-
24
-
-
0002746107
-
-
and references therein
-
The absolute stereochemistry of cyclopropane 10a was assigned as 1R,2R by comparison of the optical rotation with literature values; see for example: Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79 and references therein.
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Adv. Synth. Catal.
, vol.343
, pp. 79
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Niimi, T.1
Uchida, T.2
Irie, R.3
Katsuki, T.4
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27
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0001713095
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Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
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Bedekar, A.V.1
Koroleva, E.B.2
Andersson, P.G.3
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0030012272
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(a) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
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Tetrahedron
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Ito, K.1
Yoshitake, M.2
Katsuki, T.3
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30
-
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1642363951
-
-
Ojima, I., Ed.; Wiley-VCH: New York, Chapter 5
-
Of note, disubstituted chiral bis(oxazoline) ligands provide improved enantioselection in AC reactions; see: Doyle, M. P. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 5.
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(2000)
Catalytic Asymmetric Synthesis, 2nd Ed.
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Doyle, M.P.1
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