-
1
-
-
0003598094
-
-
Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt
-
(a) Seebach, D. In Modern Synthetic Methods; Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt, 1980.
-
(1980)
Modern Synthetic Methods
-
-
Seebach, D.1
-
2
-
-
33845373528
-
-
(b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6071
-
-
Kitamura, M.1
Suga, S.2
Kawai, K.3
Noyori, R.4
-
3
-
-
0042112714
-
-
(c) Shibasaki, M.; Nishikimi, Y.; Iimori, T.; Sodeoka, M. J. Org. Chem. 1989, 64, 3354.
-
(1989)
J. Org. Chem.
, vol.64
, pp. 3354
-
-
Shibasaki, M.1
Nishikimi, Y.2
Iimori, T.3
Sodeoka, M.4
-
4
-
-
0025674235
-
-
(d) Sugiyama, T.; Murayama, T.; Yamashita, K. Tetrahedron Lett. 1990, 31, 7343.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 7343
-
-
Sugiyama, T.1
Murayama, T.2
Yamashita, K.3
-
6
-
-
0029993774
-
-
(f) Yamamoto, Y.; Kin, H.; Suzuki, I.; Asao, N. Tetrahedron Lett. 1996, 37, 1863.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 1863
-
-
Yamamoto, Y.1
Kin, H.2
Suzuki, I.3
Asao, N.4
-
7
-
-
0030670394
-
-
(g) Wood, J. L.; Stolz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9641
-
-
Wood, J.L.1
Stolz, B.M.2
Dietrich, H.J.3
Pflum, D.A.4
Petsch, D.T.5
-
9
-
-
0030895728
-
-
(i) Kirschning, A.; Drager, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 253
-
-
Kirschning, A.1
Drager, G.2
Jung, A.3
-
11
-
-
0032481328
-
-
(k) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 708
-
-
Adam, W.1
Fell, R.T.2
Stegmann, V.R.3
Saha-Moller, C.R.4
-
12
-
-
0030952586
-
-
(l) Evans, D. A.; Kozlowski, M. C.; Burgey, S. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 1998, 119, 7893.
-
(1998)
J. Am. Chem. Soc.
, vol.119
, pp. 7893
-
-
Evans, D.A.1
Kozlowski, M.C.2
Burgey, S.C.3
MacMillan, D.W.C.4
-
13
-
-
0033603378
-
-
(m) Barbaro, G.; Battaglia, A.; Guerrini, A. J. Org. Chem. 1999, 64, 4643-4651.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 4643-4651
-
-
Barbaro, G.1
Battaglia, A.2
Guerrini, A.3
-
14
-
-
0013533832
-
-
(a) Bugno, C.; Colombani, S. M.; Dapporto, P.; Garelli, G.; Giorgi, P.; Subissi, A.; Turbanti, L. Chirality 1997, 721.
-
(1997)
Chirality
, pp. 721
-
-
Bugno, C.1
Colombani, S.M.2
Dapporto, P.3
Garelli, G.4
Giorgi, P.5
Subissi, A.6
Turbanti, L.7
-
15
-
-
0017710762
-
-
(b) Atkinson, E. R.; McRitchi, D. D.; Schoer, L. F. J. Med. Chem. 1997, 20, 1612.
-
(1997)
J. Med. Chem.
, vol.20
, pp. 1612
-
-
Atkinson, E.R.1
McRitchi, D.D.2
Schoer, L.F.3
-
16
-
-
0025289473
-
-
(a) Caldwell, C. G.; Rupprecht, K. M.; Bondy, S. S.; Davia, A. A. J. Org. Chem. 1990, 55, 2355.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2355
-
-
Caldwell, C.G.1
Rupprecht, K.M.2
Bondy, S.S.3
Davia, A.A.4
-
17
-
-
84889398397
-
-
(b) Boeckman, R. K., Jr.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 9682
-
-
Boeckman R.K., Jr.1
Yoon, S.K.2
Heckendorn, D.K.3
-
18
-
-
0026495370
-
-
(c) Yamada, K.; Niwa, H.; Ogawa, T.; Okamoto, O. Tetrahedron 1992, 48, 10531.
-
(1992)
Tetrahedron
, vol.48
, pp. 10531
-
-
Yamada, K.1
Niwa, H.2
Ogawa, T.3
Okamoto, O.4
-
21
-
-
0029265229
-
-
Yarker, Y. E.; Goa, K. L.; Fitton, A. Drug Aging 1995, 6, 243.
-
(1995)
Drug Aging
, vol.6
, pp. 243
-
-
Yarker, Y.E.1
Goa, K.L.2
Fitton, A.3
-
22
-
-
0033613779
-
-
Senanayake, C. H.; Fang, Q. K.; Grover, P.; Bakale, R. P.; Vandenbossche, C. P.; Wald, S. A. Tetrahedron Lett. 1999, 40, 819-822.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 819-822
-
-
Senanayake, C.H.1
Fang, Q.K.2
Grover, P.3
Bakale, R.P.4
Vandenbossche, C.P.5
Wald, S.A.6
-
23
-
-
0030513164
-
-
(a) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 2708-2748
-
-
Seebach, D.1
Sting, A.R.2
Hoffmann, M.3
-
24
-
-
0003129117
-
-
Scheffold, R., Ed.; Salle+Sauerlander: Aarau
-
(b) Seebach, D.; Hungerbuhler E. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle+Sauerlander: Aarau, 1980; Vol. 2, pp 91-171.
-
(1980)
Modern Synthetic Methods
, vol.2
, pp. 91-171
-
-
Seebach, D.1
Hungerbuhler, E.2
-
25
-
-
0025931951
-
-
(a) Carter, P. J.; Blob, L.; Audia, V. A.; Dupont, A. C.; McPherson, D. W.; Natalie, K. J., Jr.; Rzeszotarski, W. J.; Spagnuolz, C. J.; Waid, P. P.; Kaiser, C. J. Med. Chem. 1991, 34, 3065.
-
(1991)
J. Med. Chem.
, vol.34
, pp. 3065
-
-
Carter, P.J.1
Blob, L.2
Audia, V.A.3
Dupont, A.C.4
McPherson, D.W.5
Natalie K.J., Jr.6
Rzeszotarski, W.J.7
Spagnuolz, C.J.8
Waid, P.P.9
Kaiser, C.10
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27
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0343778312
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2CCHO were also examined. However, the diastereoselectivity in the preparation of these dioxolones was poor
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2CCHO were also examined. However, the diastereoselectivity in the preparation of these dioxolones was poor.
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(1984)
Tetrahedron
, pp. 40
-
-
Seebach, D.1
Naef, R.2
Calderari, G.3
-
29
-
-
0042552592
-
-
(b) Polonski, T. Tetrahedron 1983, 39, 3131. Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1881.
-
(1983)
Tetrahedron
, vol.39
, pp. 3131
-
-
Polonski, T.1
-
30
-
-
0343778311
-
-
(b) Polonski, T. Tetrahedron 1983, 39, 3131. Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1881.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1881
-
-
Ortholand, J.-Y.1
Vicart, N.2
Greiner, A.3
-
31
-
-
0000578396
-
-
(c) Frater, G.; Muller, U.; Gunther, W. Tetrahedron Lett. 1981, 22, 4221.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 4221
-
-
Frater, G.1
Muller, U.2
Gunther, W.3
-
32
-
-
0001647522
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-
(d) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 1351
-
-
Hoye, T.R.1
Peterson, B.H.2
Miller, J.D.3
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33
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0342473207
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note
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4 provided reasonable selectivities from 90:10 to 94:6. matrix presented
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34
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0343342665
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Using 1.1 equiv of pivaldehyde is ideal for the reaction. Using more equivalents of aldehyde results in formation of the trimer byproduct 10; see Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1998, 120, 984.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 984
-
-
Denmark, S.E.1
Wilson, T.2
Willson, T.M.3
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35
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0342473210
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note
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5 according to Scheme 3, path a.
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-
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36
-
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0342907570
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The reaction was performed at -100 °C; however the rate of reaction was greatly reduced and the selectivity was not improved
-
The reaction was performed at -100 °C; however the rate of reaction was greatly reduced and the selectivity was not improved.
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-
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37
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0342907571
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Heating to higher temperatures (>0 °C) results in some decomposition
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Heating to higher temperatures (>0 °C) results in some decomposition.
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40
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0342473206
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(c) Taguchi, H.; Yamamoto, H.; Nozaki, H. Tetradedron Lett. 1973, 27, 2463.
-
(1973)
Tetradedron Lett.
, vol.27
, pp. 2463
-
-
Taguchi, H.1
Yamamoto, H.2
Nozaki, H.3
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45
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0029883221
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(h) Campbell, E.; Martin, J. J.; Bordner, J.; Kleinman, E. F. J. Org. Chem. 1996, 61, 4806.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4806
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Campbell, E.1
Martin, J.J.2
Bordner, J.3
Kleinman, E.F.4
-
47
-
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0342473209
-
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note
-
(a) To obtain a clean reaction product, the order of addition of thionyl chloride and pyridine is essential. Thionyl chloride is added first, followed by pyridine. (b) A mild wash with aqueous ammonium chloride is necessary to remove sulfur impurities, which can poison Pd/C and render the hydrogenation to (S)-1 ineffective.
-
-
-
-
48
-
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0342907569
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note
-
Alkylation of (S,S)-2 with cyclohexyl iodide was unsuccessful. The more expensive 3-bromocyclohexene undergoes smooth alkylation to provide the alkylated adduct in 77% yield with >98:2 selectivity, which after hydrogenation followed by hydrolysis provides (S)-1 in 97% ee in high yields. This alkylation chemistry is a facile entry to (S)-1. However, the availability of the bromocyclohexenyl in large scale limits practicality. matrix presented
-
-
-
-
49
-
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0343778302
-
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The stereochemical assignments of 7, 8, and 9, respectively, were predicated in an analogus manner to the (S)-1 as discussed in ref 12b
-
The stereochemical assignments of 7, 8, and 9, respectively, were predicated in an analogus manner to the (S)-1 as discussed in ref 12b.
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