-
2
-
-
43149108403
-
-
For recent contributions, see:
-
For recent contributions, see:
-
-
-
-
4
-
-
36349033298
-
-
Christmann M., and Bräse S. (Eds), Wiley-VCH, Weinheim Part I
-
Evans D.A., Helmchen G., Rüping M., Brückner R., Davis F.A., Enders D., Bettray W., Hoffmann R.W., Kunz H., Meyers A.I., Murahashi S.-I., and Imada Y. In: Christmann M., and Bräse S. (Eds). Asymmetric Synthesis-The Essentials (2008), Wiley-VCH, Weinheim 3-47 Part I
-
(2008)
Asymmetric Synthesis-The Essentials
, pp. 3-47
-
-
Evans, D.A.1
Helmchen, G.2
Rüping, M.3
Brückner, R.4
Davis, F.A.5
Enders, D.6
Bettray, W.7
Hoffmann, R.W.8
Kunz, H.9
Meyers, A.I.10
Murahashi, S.-I.11
Imada, Y.12
-
10
-
-
0000665968
-
-
Nagao Y., Hagiwara Y., Kumagai T., Ochiai M., Inoue T., Hashimoto K., and Fujita E. J. Org. Chem. 51 (1986) 2391
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(1986)
J. Org. Chem.
, vol.51
, pp. 2391
-
-
Nagao, Y.1
Hagiwara, Y.2
Kumagai, T.3
Ochiai, M.4
Inoue, T.5
Hashimoto, K.6
Fujita, E.7
-
16
-
-
43149086887
-
-
For similar processes based on N-acetyl-1,3-oxazolidine-2-thiones, see:
-
For similar processes based on N-acetyl-1,3-oxazolidine-2-thiones, see:
-
-
-
-
17
-
-
0001243425
-
-
Yan T.-H., Hung A.-W., Lee H.-C., Chang C.-S., and Liu W.-H. J. Org. Chem. 60 (1995) 3301
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3301
-
-
Yan, T.-H.1
Hung, A.-W.2
Lee, H.-C.3
Chang, C.-S.4
Liu, W.-H.5
-
19
-
-
43149104422
-
-
For recent reviews on the synthesis and reactivity of chiral oxazolidinethiones and thiazolidinethiones, see:
-
For recent reviews on the synthesis and reactivity of chiral oxazolidinethiones and thiazolidinethiones, see:
-
-
-
-
22
-
-
0001583042
-
-
Cosp A., Romea P., Talavera P., Urpí F., Vilarrasa J., Font-Bardia M., and Solans X. Org. Lett. 3 (2001) 615
-
(2001)
Org. Lett.
, vol.3
, pp. 615
-
-
Cosp, A.1
Romea, P.2
Talavera, P.3
Urpí, F.4
Vilarrasa, J.5
Font-Bardia, M.6
Solans, X.7
-
24
-
-
43149096523
-
-
For the preparation of thiazolidinethione-like chiral auxiliaries, see:
-
For the preparation of thiazolidinethione-like chiral auxiliaries, see:
-
-
-
-
26
-
-
43149124868
-
-
See Ref. 10.
-
See Ref. 10.
-
-
-
-
27
-
-
43149119288
-
-
note
-
2 was chosen because its milder character as Lewis acid.
-
-
-
-
28
-
-
43149087822
-
-
note
-
Crystallographic data (excluding structure factors) for this structure has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-150269. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
-
-
-
-
29
-
-
0141520591
-
-
For a structural study on these adducts, see:
-
For a structural study on these adducts, see:. Cosp A., Larrosa I., Anglada J.M., Bofill J.M., Romea P., and Urpí F. Org. Lett. 5 (2003) 2809
-
(2003)
Org. Lett.
, vol.5
, pp. 2809
-
-
Cosp, A.1
Larrosa, I.2
Anglada, J.M.3
Bofill, J.M.4
Romea, P.5
Urpí, F.6
-
30
-
-
0003942864
-
-
-1) on the basis of the different conformational arrangements available for the alternative transition states (for a nice discussion, see:
-
-1) on the basis of the different conformational arrangements available for the alternative transition states (for a nice discussion, see:
-
(1994)
Stereochemistry of Organic Compounds
-
-
Eliel, E.L.1
Wilen, S.H.2
-
31
-
-
0000784039
-
-
2 relies on kinetic grounds, it may be helpful to consider the phenyl group as the smallest substituent positioned at C4 in the N-propanoyl thiazolidinethiones 3
-
2 relies on kinetic grounds, it may be helpful to consider the phenyl group as the smallest substituent positioned at C4 in the N-propanoyl thiazolidinethiones 3
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4151
-
-
Roush, W.R.1
-
32
-
-
43149099024
-
-
note
-
For the effect of the C4 substituent of such chiral auxiliaries in the context of the acetate aldol reaction, see Ref. 8b.
-
-
-
-
33
-
-
37549023756
-
-
An excellent analysis on the steric bulk of the C4 substituent in the addition of the titanium enolates from N-acetyl-1,3-thiazolidine-2-thiones to dimethyl acetals in the course of the total synthesis of (-)-hennoxazole has been recently reported, see:
-
An excellent analysis on the steric bulk of the C4 substituent in the addition of the titanium enolates from N-acetyl-1,3-thiazolidine-2-thiones to dimethyl acetals in the course of the total synthesis of (-)-hennoxazole has been recently reported, see:. Smith T.E., Kuo W.-H., Balskus E.P., Bock V.D., Roizen J.L., Theberge A.B., Carroll K.A., Kurihara T., and Wessler J.D. J. Org. Chem. 73 (2008) 142
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(2008)
J. Org. Chem.
, vol.73
, pp. 142
-
-
Smith, T.E.1
Kuo, W.-H.2
Balskus, E.P.3
Bock, V.D.4
Roizen, J.L.5
Theberge, A.B.6
Carroll, K.A.7
Kurihara, T.8
Wessler, J.D.9
-
34
-
-
43149087566
-
-
Lewis acid-mediated additions of carbon nucleophiles to acetals usually proceed through carbocation intermediates. For example, see:
-
Lewis acid-mediated additions of carbon nucleophiles to acetals usually proceed through carbocation intermediates. For example, see:
-
-
-
-
37
-
-
0030973398
-
-
Matsutani H., Ichikawa S., Yaruva J., Kusumoto T., and Hiyama T. J. Am. Chem. Soc. 119 (1997) 4541
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(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4541
-
-
Matsutani, H.1
Ichikawa, S.2
Yaruva, J.3
Kusumoto, T.4
Hiyama, T.5
-
39
-
-
0001151568
-
-
and references therein
-
Mori I., Ishihara K., Flippin L.A., Nozaki K., Yamamoto H., Bartlett P.A., and Heathcock C.H. J. Org. Chem. 55 (1990) 6107 and references therein
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(1990)
J. Org. Chem.
, vol.55
, pp. 6107
-
-
Mori, I.1
Ishihara, K.2
Flippin, L.A.3
Nozaki, K.4
Yamamoto, H.5
Bartlett, P.A.6
Heathcock, C.H.7
-
40
-
-
43149121834
-
-
Unpublished results from Erik Galvez, Ph.D. Thesis in course.
-
Unpublished results from Erik Galvez, Ph.D. Thesis in course.
-
-
-
-
41
-
-
0000693134
-
-
N2 mechanism. For a nice account on this issue, see:
-
N2 mechanism. For a nice account on this issue, see:. Denmark S.E., and Almstead N.G. J. Am. Chem. Soc. 113 (1991) 8089
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 8089
-
-
Denmark, S.E.1
Almstead, N.G.2
-
42
-
-
43149084624
-
-
For related examples on the influence of C4 substituents on the structure of several enolates, see:
-
For related examples on the influence of C4 substituents on the structure of several enolates, see:
-
-
-
-
44
-
-
0034699412
-
-
Bull S.D., Davies S.G., Key M.-S., Nicholson R.L., and Savory E.D. Chem. Commun. (2000) 1721
-
(2000)
Chem. Commun.
, pp. 1721
-
-
Bull, S.D.1
Davies, S.G.2
Key, M.-S.3
Nicholson, R.L.4
Savory, E.D.5
-
45
-
-
2142757265
-
-
For the crucial role played by the exocyclic sulfur atom in the addition of titanium enolates from N-acetyl-1,3-oxazolidine-2-thiones to 2,5-disubstituted tetrahydrofurans, see:
-
For the crucial role played by the exocyclic sulfur atom in the addition of titanium enolates from N-acetyl-1,3-oxazolidine-2-thiones to 2,5-disubstituted tetrahydrofurans, see:. Jalce G., Seck M., Franck X., Hocquemiller R., and Figadère B. J. Org. Chem. 69 (2004) 3240
-
(2004)
J. Org. Chem.
, vol.69
, pp. 3240
-
-
Jalce, G.1
Seck, M.2
Franck, X.3
Hocquemiller, R.4
Figadère, B.5
-
47
-
-
0035815117
-
-
Cuzzupe A.N., Hutton C.A., Lilly M.J., Mann R.K., McRae K.J., Zammit S.C., and Rizzacasa M.A. J. Org. Chem. 66 (2001) 2382
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(2001)
J. Org. Chem.
, vol.66
, pp. 2382
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-
Cuzzupe, A.N.1
Hutton, C.A.2
Lilly, M.J.3
Mann, R.K.4
McRae, K.J.5
Zammit, S.C.6
Rizzacasa, M.A.7
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