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0342747434
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note
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In a control experiment, (R)-34 (95% ee) was treated with the same ratio of diamine 1a + lithioamide 5 that would be present after enolate protonation in THF prior to workup. After 10 min at 0°C, the mixture was allowed to warm to 20°C and was then quenched in the usual way to give 4c with 31% ee, indicating partial racemization.
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0017324475
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De Oliveira Baptista, M. J. V.; Barrett A. G. M.; Barton, D. H. R.; Girijavallubhan, M.; Jennings, R. C.; Kelly, J.; Papadimitriou, V. J.; Turner, J. V.; Usher, N. A. J. Chem. Soc., Perkin Trans. 1 1977, 1477.
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De Oliveira Baptista, M.J.V.1
Barrett, A.G.M.2
Barton, D.H.R.3
Girijavallubhan, M.4
Jennings, R.C.5
Kelly, J.6
Papadimitriou, V.J.7
Turner, J.V.8
Usher, N.A.9
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29
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85004388152
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Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475. Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1990, 31, 5507.
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Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475. Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1990, 31, 5507.
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31
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0342312537
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note
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A hydrazide corresponding to 7, but derived from N,N′-diisopropylhydrazine could also be deracemized. Because of the presence of an N-H subunit, a temporary blocking procedure was used as follows: N-H lithiation with 1 equiv of n-BuLi; N-silylation with TMSC1 (1 equiv) at -78°C; enolate formation with 2 equiv of n-BuLi; protonation with 1a, and quenching as usual. The recovered hydrazide after aqueous workup was formed with 69-72% ee.
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32
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0343617465
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note
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Prepared from the known carboxylic acids (ref 13) via the acid chloride and diisopropylamine; see the Experimental Section.
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34
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0005196361
-
-
(b) 12: Black, T. H.; Eisenbeis, S. A.; McDermott, T. S.; Maluleka, S. L.; Tetrahedron 1990, 46, 2307.
-
(1990)
Tetrahedron
, vol.46
, pp. 2307
-
-
Black, T.H.1
Eisenbeis, S.A.2
McDermott, T.S.3
Maluleka, S.L.4
-
35
-
-
0342353987
-
-
(c) 14c: Henin, F.; Mortezaei, R.; Muzart, J.; Pete, J. P.; Piva, O. Tetrahedron 1989, 45, 6171.
-
(1989)
Tetrahedron
, vol.45
, pp. 6171
-
-
Henin, F.1
Mortezaei, R.2
Muzart, J.3
Pete, J.P.4
Piva, O.5
-
39
-
-
0342312523
-
-
note
-
The absolute configuration is assigned by analogy to (R)-10.
-
-
-
-
40
-
-
84918717463
-
-
Van Bekkum, H.; Van den Bosch, C. B.; Van Minnen-Pathuis, G.; De Mos, J. C.; Van Wijk, A. M. Recl. Trav. Chim. Pays-Bas 1971, 90, 137.
-
(1971)
Recl. Trav. Chim. Pays-Bas
, vol.90
, pp. 137
-
-
Van Bekkum, H.1
Van Den Bosch, C.B.2
Van Minnen-Pathuis, G.3
De Mos, J.C.4
Van Wijk, A.M.5
-
42
-
-
0343617460
-
-
note
-
Absolute configuration not assigned.
-
-
-
-
44
-
-
33845551868
-
-
Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390. Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 5390
-
-
Seebach, D.1
Boes, M.2
Naef, R.3
Schweizer, W.B.4
-
45
-
-
0000598748
-
-
Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390. Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 105
-
-
Hogeveen, H.1
Zwart, L.2
-
46
-
-
0001672561
-
-
Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391. Kresz, G.; Runge, E.; Ruch, E. Justus Liebigs Ann. Chem. 1972, 756, 112.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 5391
-
-
Baigrie, L.M.1
Seiklay, H.R.2
Tidwell, T.T.3
-
47
-
-
84983038183
-
-
Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391. Kresz, G.; Runge, E.; Ruch, E. Justus Liebigs Ann. Chem. 1972, 756, 112.
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(1972)
Justus Liebigs Ann. Chem.
, vol.756
, pp. 112
-
-
Kresz, G.1
Runge, E.2
Ruch, E.3
-
48
-
-
0342312516
-
-
note
-
3 signal upfield relative to the E-isomer). The assignment was confirmed in the case of the enol silanes derived from 4a by an NOE experiment. In contrast to the major enol silanes derived from 4a and from 9b, the major enol silane isomer from 9a has a downfield chemical shift (δ 0.253 ppm, major, vs -0.122 ppm, minor), suggesting that this may be the E-enol silane 23a-E. A definitive assignment could not be made using NOE methods.
-
-
-
-
49
-
-
0343182080
-
-
note
-
This value was determined by Bordwell and Satish; see ref 7.
-
-
-
-
50
-
-
84990085779
-
-
Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhayay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
-
(1988)
Angew. Chem., Int. Ed. Engl.
, vol.27
, pp. 1624
-
-
Seebach, D.1
-
51
-
-
0027370981
-
-
Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhayay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
-
(1993)
Synthesis
, pp. 1271
-
-
Juaristi, E.1
Beck, A.K.2
Hansen, J.3
Matt, T.4
Mukhopadhayay, T.5
Simson, M.6
Seebach, D.7
-
53
-
-
0030500535
-
-
(a) Kresge, A. J. Chem. Soc. Rev. 1996, 25, 275. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
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(1996)
Chem. Soc. Rev.
, vol.25
, pp. 275
-
-
Kresge, A.J.1
-
54
-
-
0002905711
-
-
(a) Kresge, A. J. Chem. Soc. Rev. 1996, 25, 275. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
-
(1990)
Acc. Chem. Res.
, vol.23
, pp. 43
-
-
Kresge, A.J.1
-
55
-
-
0009673198
-
-
(b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
-
(1981)
Angew. Chem.
, vol.93
, pp. 1007
-
-
Seebach, D.1
Wasmuth, D.2
-
56
-
-
0345022255
-
-
(b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 9694
-
-
Kawabata, T.1
Yahiro, K.2
Fuji, K.3
-
57
-
-
0001694916
-
-
(b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
-
(1998)
Chem. Eur. J.
, vol.4
, pp. 373
-
-
Fuji, K.1
Kawabata, T.2
-
58
-
-
0030583467
-
-
(b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 7607
-
-
Hughes, A.D.1
Price, D.A.2
Shishkin, O.3
Simpkins, N.S.4
-
59
-
-
0343182034
-
-
Ott, H.; Hardtmann, G.; Denzer, M.; Frey, A. J.; Gogerty, J. H.; Leslie, G. H.; Trapold, J. H. J. Med. Chem. 1968, 11, 7.
-
(1968)
J. Med. Chem.
, vol.11
, pp. 7
-
-
Ott, H.1
Hardtmann, G.2
Denzer, M.3
Frey, A.J.4
Gogerty, J.H.5
Leslie, G.H.6
Trapold, J.H.7
-
60
-
-
0039570354
-
-
Zinner, G.; Kliegel, W.; Ritter, W.; Bölke, H. Chem. Ber. 1966, 99, 1678.
-
(1966)
Chem. Ber.
, vol.99
, pp. 1678
-
-
Zinner, G.1
Kliegel, W.2
Ritter, W.3
Bölke, H.4
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