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0042733174
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Reviews: a) R. L. Subramanian, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E19d, 1993, pp. 744-754; b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 865; c) J.-F. Normant, Chemtracts: Org. Chem. 1994, 7, 59-73.
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Subramanian, R.L.1
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2
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0001522634
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Eds.: B. M. Trost, I. Fleming, Pergamon, New York
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Reviews: a) R. L. Subramanian, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E19d, 1993, pp. 744-754; b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 865; c) J.-F. Normant, Chemtracts: Org. Chem. 1994, 7, 59-73.
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Comprehensive Organic Synthesis
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Knochel, P.1
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3
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0002449911
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Reviews: a) R. L. Subramanian, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E19d, 1993, pp. 744-754; b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 865; c) J.-F. Normant, Chemtracts: Org. Chem. 1994, 7, 59-73.
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Normant, J.-F.1
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4
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0010594945
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a) V. N. Drozd, U. A. Ustynyuk, M. A. Tsel'eva, L. B. Dmitriev, J. Gen. Chem. USSR 1968, 38, 2047; Zh. Obsch. Khan. 1968, 38, 2144;
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J. Gen. Chem. USSR
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Drozd, V.N.1
Ustynyuk, U.A.2
Tsel'eva, M.A.3
Dmitriev, L.B.4
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5
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84912964962
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a) V. N. Drozd, U. A. Ustynyuk, M. A. Tsel'eva, L. B. Dmitriev, J. Gen. Chem. USSR 1968, 38, 2047; Zh. Obsch. Khan. 1968, 38, 2144;
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Zh. Obsch. Khan.
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6
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33746458511
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b) W. F. Bailey, T. T. Nurmi, J. J. Patricia, W. Wang, J. Am. Chem. Soc. 1987, 109, 2442-2448;
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J. Am. Chem. Soc.
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Bailey, W.F.1
Nurmi, T.T.2
Patricia, J.J.3
Wang, W.4
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7
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-
0028260787
-
-
and references therein
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c) W. F. Bailey, K. V. Gavaskar, Tetrahedron 1994, 50, 5957-5970, and references therein;
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(1994)
Tetrahedron
, vol.50
, pp. 5957-5970
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-
Bailey, W.F.1
Gavaskar, K.V.2
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8
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-
0007884867
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-
and references therein
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d) A. Krief, J. Bousbaa, Synlett 1996, 1007-1009, and references therein.
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Synlett
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Krief, A.1
Bousbaa, J.2
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9
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0001493946
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S. Klein, I. Marek, J.-F. Poisson, J.-F. Normant, J. Am. Chem. Soc. 1995, 117, 8853-8854.
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Klein, S.1
Marek, I.2
Poisson, J.-F.3
Normant, J.-F.4
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10
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0001488536
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a) D. Hoppe, F. Hintze. P. Tebben, Angew. Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Eng. 1990, 29, 1422-1423;
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Angew. Chem.
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Hoppe, D.1
Hintze, F.2
Tebben, P.3
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11
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0343583098
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a) D. Hoppe, F. Hintze. P. Tebben, Angew. Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Eng. 1990, 29, 1422-1423;
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Angew. Chem. Int. Ed. Eng.
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-
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12
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0344799549
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-
b) short review: D. Hoppe, F. Hintze, P. Tebben, M. Paetow, H. Ahrens, J. Schwerdtfeger, P. Sommerfeld, J. Haller, W. Guarnieri, S. Kolczewski, T. Hense, I. Hoppe, Pure Appl. Chem. 1994, 66, 1479-1486.
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Hoppe, D.1
Hintze, F.2
Tebben, P.3
Paetow, M.4
Ahrens, H.5
Schwerdtfeger, J.6
Sommerfeld, P.7
Haller, J.8
Guarnieri, W.9
Kolczewski, S.10
Hense, T.11
Hoppe, I.12
-
13
-
-
0642329707
-
-
note
-
2O, reflux, 1 h, then aldehyde (6), RT. 15 h, 1b: 81% (Z:E = 46:54).
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-
-
-
15
-
-
0642299137
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-
note
-
3Si (465.709): C 72.21, H 8.44, N 3.01; found: C 72.29, H 8.49, N 3.26.
-
-
-
-
16
-
-
0642329708
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-
note
-
The crude carboxylic acid was converted into the methyl ester 5g by treatment with diazomethane. A small amount of the carboxylate presumably epimerizes under the work-up conditions.
-
-
-
-
17
-
-
0642329711
-
-
note
-
3 to be greater than 95%.
-
-
-
-
18
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-
0642299138
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-
note
-
The by-products of the reactions of la were the corresponding open-chain substitution product and the cyclopropane derivative resulting from intramolecular 1,3-elimination of the carbamate group. Reactions of 1b delivered the cyclopropane derivative as well as the substrate. Therefore, in case of 1a the yields are limited either by the rate of cyclization or the unfavorable equilibrium constant, whereas for 1b the slow deprotonation step plays a crucial role. Other by-products were not identified.
-
-
-
-
20
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-
0642360407
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-
note
-
D = -46.8 (c = 1.10 in MeOH)[11]).
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-
-
-
21
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0000276453
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-
a) K. Tamao, N. Ishida, T. Tanaka, M. Kumuda, Organometallics 1983, 2, 1694-1696;
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(1983)
Organometallics
, vol.2
, pp. 1694-1696
-
-
Tamao, K.1
Ishida, N.2
Tanaka, T.3
Kumuda, M.4
-
22
-
-
0642299140
-
-
b) K. Tamao, T. Tanaka, T. Nakajima, R. Sumiya, H. Arai, Y. Ito, Tetrahedron Lett. 1986, 27, 3370-3380;
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(1986)
Tetrahedron Lett.
, vol.27
, pp. 3370-3380
-
-
Tamao, K.1
Tanaka, T.2
Nakajima, T.3
Sumiya, R.4
Arai, H.5
Ito, Y.6
-
24
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-
37049088928
-
-
d) I. Fleming, R. Henning, D. C. Parker, H. E. Plaut, P. E. J. Sanderson, J. Chem. Soc. Perkin Trans. 1 1995, 317-337;
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J. Chem. Soc. Perkin Trans. 1
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-
-
Fleming, I.1
Henning, R.2
Parker, D.C.3
Plaut, H.E.4
Sanderson, P.E.J.5
-
25
-
-
0027958642
-
-
and references therein
-
e) Y. Matsumoto, T. Hayashi, Y. Ho, Tetrahedron 1994, 50, 335-346, and references therein.
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(1994)
Tetrahedron
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-
-
Matsumoto, Y.1
Hayashi, T.2
Ho, Y.3
-
26
-
-
0642268451
-
-
note
-
Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 367. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code +(1223)336-033; e-mail; deposit@chemcrys.cam.ac.uk).
-
-
-
-
27
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-
0001317003
-
-
a) D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1455-1456; Angew. Chem. Int. Ed. Eng. 1990, 29, 1424-1425;
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(1990)
Angew. Chem.
, vol.102
, pp. 1455-1456
-
-
Hoppe, D.1
Carstens, A.2
Krämer, T.3
-
28
-
-
0343177680
-
-
a) D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1455-1456; Angew. Chem. Int. Ed. Eng. 1990, 29, 1424-1425;
-
(1990)
Angew. Chem. Int. Ed. Eng.
, vol.29
, pp. 1424-1425
-
-
-
30
-
-
0642268450
-
-
note
-
However, protonations occur under retention of configuration [15,17]. Therefore, for E1 = H the other benzylic epimer must be generated. As this is not of any significance for the examples described in here, the structure of 1′-epi-5 is not shown.
-
-
-
-
32
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0000679903
-
-
P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560.
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(1996)
Acc. Chem. Res.
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-
-
Beak, P.1
Basu, A.2
Gallagher, D.J.3
Park, Y.S.4
Thayumanavan, S.5
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