-
1
-
-
84934495642
-
-
Bernardi, F, Csizmadia, I. G, Mangini, A, Eds, Elsevier: Amsterdam, Chapter 5
-
(a) Capozzi, G.; Modena, G. In Organic Sulfur Chemistry; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; Chapter 5.
-
(1985)
Organic Sulfur Chemistry
-
-
Capozzi, G.1
Modena, G.2
-
5
-
-
33749431997
-
-
(e) Braga, A. L.; Lüdtke, D. S.; Vargas, F. Curr. Org. Chem. 2006, 10, 1921-1938.
-
(2006)
Curr. Org. Chem
, vol.10
, pp. 1921-1938
-
-
Braga, A.L.1
Lüdtke, D.S.2
Vargas, F.3
-
7
-
-
13444267885
-
-
An important exception is the enantioselective functionalization of aldehydes with sulfur and selenium electrophiles, catalyzed by chiral amines (via their enamines, a) Marigo, M, Wabnitz, T. C, Fielenbach, D, Jørgensen, K. A. Angew. Chem, Int. Ed. 2005, 44, 794-797
-
An important exception is the enantioselective functionalization of aldehydes with sulfur and selenium electrophiles, catalyzed by chiral amines (via their enamines). (a) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794-797.
-
-
-
-
8
-
-
29844457732
-
-
(b) Franzn, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjærsgaard, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296-18304.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 18296-18304
-
-
Franzn, J.1
Marigo, M.2
Fielenbach, D.3
Wabnitz, T.C.4
Kjærsgaard, A.5
Jørgensen, K.A.6
-
9
-
-
34548764427
-
-
(c) Tiecco, M.; Carlone, A.; Sternativo, S.; Marini, F.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 6882-6885.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 6882-6885
-
-
Tiecco, M.1
Carlone, A.2
Sternativo, S.3
Marini, F.4
Bartoli, G.5
Melchiorre, P.6
-
10
-
-
54249164455
-
-
Zhao, G.-L.; Rios, R.; Vesely, J.; Eriksson, L.; Cordova, A. Angew. Chem., Int. Ed. 2008, 47, 8468-8472. See also:
-
(d) Zhao, G.-L.; Rios, R.; Vesely, J.; Eriksson, L.; Cordova, A. Angew. Chem., Int. Ed. 2008, 47, 8468-8472. See also:
-
-
-
-
11
-
-
0001403969
-
-
(e) Fukuzawa, S.-I.; Takahashi, K.; Kato, H.; Yamazaki, H. J. Org. Chem. 1997, 62, 7711-7716.
-
(1997)
J. Org. Chem
, vol.62
, pp. 7711-7716
-
-
Fukuzawa, S.-I.1
Takahashi, K.2
Kato, H.3
Yamazaki, H.4
-
12
-
-
0345195997
-
-
(f) Wirth, T.; Haüptli, S.; Leuenberger, M. Tetrahedron: Asymmetry 1998, 9, 547-550.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 547-550
-
-
Wirth, T.1
Haüptli, S.2
Leuenberger, M.3
-
15
-
-
50249134990
-
-
(c) Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 1560-1638
-
-
Denmark, S.E.1
Beutner, G.L.2
-
16
-
-
77957045994
-
-
Rayner, C. M. In Organosulfur Chemistry: Synthetic Aspects; Bullman- Page, P., Ed.; Academic Press: London, 1995; pp 89-131.
-
(a) Rayner, C. M. In Organosulfur Chemistry: Synthetic Aspects; Bullman- Page, P., Ed.; Academic Press: London, 1995; pp 89-131.
-
-
-
-
17
-
-
33845561243
-
-
(b) Smit, W. A.; Zefirov, N. S.; Bodrikov, I. V.; Krimer, M. Z. Acc. Chem. Res. 1979, 12, 282-288.
-
(1979)
Acc. Chem. Res
, vol.12
, pp. 282-288
-
-
Smit, W.A.1
Zefirov, N.S.2
Bodrikov, I.V.3
Krimer, M.Z.4
-
18
-
-
70149086322
-
-
Schmid, G. H.; Garratt, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, pp 854-866.
-
(c) Schmid, G. H.; Garratt, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, pp 854-866.
-
-
-
-
21
-
-
0000226222
-
-
(a) Lucchini, V.; Modena, G.; Pasquato, L. Gazz. Chim. Ital. 1997, 127, 177-188.
-
(1997)
Gazz. Chim. Ital
, vol.127
, pp. 177-188
-
-
Lucchini, V.1
Modena, G.2
Pasquato, L.3
-
23
-
-
0033475323
-
-
(c) Pasquato, L.; Destro, R.; Lucchini, V.; Modena, G. Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 153, 235-245.
-
(1999)
Phosphorus, Sulfur, Silicon Relat. Elem
, vol.153
, pp. 235-245
-
-
Pasquato, L.1
Destro, R.2
Lucchini, V.3
Modena, G.4
-
25
-
-
0005671593
-
-
(e) Capozzi, G.; De Lucchi, O.; Lucchini, V.; Modena, G. Tetrahedron Lett. 1975, 30, 2603-2604.
-
(1975)
Tetrahedron Lett
, vol.30
, pp. 2603-2604
-
-
Capozzi, G.1
De Lucchi, O.2
Lucchini, V.3
Modena, G.4
-
26
-
-
0033611941
-
-
(f) Fachini, M.; Lucchini, V.; Modena, G.; Pasi, M.; Pasquato, L. J. Am. Chem. Soc. 1999, 121, 3944-3950.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 3944-3950
-
-
Fachini, M.1
Lucchini, V.2
Modena, G.3
Pasi, M.4
Pasquato, L.5
-
29
-
-
70149096481
-
-
Borodkin, G. I.; Gatilov, Y. V.; Chernyak, E. I.; Shubin, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 2826; 1985, 34, 2622 (Engl. Transl.).
-
(a) Borodkin, G. I.; Gatilov, Y. V.; Chernyak, E. I.; Shubin, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 2826; 1985, 34, 2622 (Engl. Transl.).
-
-
-
-
30
-
-
0001663310
-
-
(b) Huang, X.; Batchelor, R. J.; Einstein, F. W. B.; Bennet, A. J. J. Org. Chem. 1994, 59, 7108-7116.
-
(1994)
J. Org. Chem
, vol.59
, pp. 7108-7116
-
-
Huang, X.1
Batchelor, R.J.2
Einstein, F.W.B.3
Bennet, A.J.4
-
31
-
-
0034596032
-
-
(c) Destro, R.; Lucchini, V.; Modena, G.; Pasquato, L. J. Org. Chem. 2000, 65, 3367-3370.
-
(2000)
J. Org. Chem
, vol.65
, pp. 3367-3370
-
-
Destro, R.1
Lucchini, V.2
Modena, G.3
Pasquato, L.4
-
32
-
-
70149118180
-
-
Borodkin, G. I.; Chernyak, E. I.; Shakirov, M. M.; Gatilov, Y. V.; Rybalova, T. V.; Shubin, V. G. Zh. Org. Khim. 1990, 26, 1163-1179; 1990, 26, 1002-1017 (Engl. Transl.).
-
(d) Borodkin, G. I.; Chernyak, E. I.; Shakirov, M. M.; Gatilov, Y. V.; Rybalova, T. V.; Shubin, V. G. Zh. Org. Khim. 1990, 26, 1163-1179; 1990, 26, 1002-1017 (Engl. Transl.).
-
-
-
-
33
-
-
0010340105
-
-
For indirect studies, see: a
-
For indirect studies, see: (a) Reetz, M. T. Pure Appl. Chem. 1988, 60, 1607- 1614.
-
(1988)
Pure Appl. Chem
, vol.60
, pp. 1607-1614
-
-
Reetz, M.T.1
-
34
-
-
0002808469
-
-
(b) Smit, W. A.; Gybin, A. S.; Bagdanov, V. S.; Krimer, M. Z.; Vorobieva, E. A. Tetrahedron Lett. 1978, 12, 1085-1088.
-
(1978)
Tetrahedron Lett
, vol.12
, pp. 1085-1088
-
-
Smit, W.A.1
Gybin, A.S.2
Bagdanov, V.S.3
Krimer, M.Z.4
Vorobieva, E.A.5
-
35
-
-
0030030819
-
-
(c) Gill, D. M.; Pegg, N. A.; Rayner, C. M. Tetrahedron 1996, 52, 3609-3630.
-
(1996)
Tetrahedron
, vol.52
, pp. 3609-3630
-
-
Gill, D.M.1
Pegg, N.A.2
Rayner, C.M.3
-
36
-
-
45549118334
-
-
(d) Capozzi, F.; Capozzi, G.; Menichetti, S. Tetrahedron Lett. 1988, 29, 4177-4180.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 4177-4180
-
-
Capozzi, F.1
Capozzi, G.2
Menichetti, S.3
-
37
-
-
0001590417
-
-
(e) Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1991, 113, 6600-6607.
-
(1991)
J. Am. Chem. Soc
, vol.113
, pp. 6600-6607
-
-
Lucchini, V.1
Modena, G.2
Pasquato, L.3
-
38
-
-
0039321123
-
-
For studies on isolated thiiranium salts, see
-
(f) Okuma, K.; Koike, T.; Yamamoto, S.; Yonekura, K; Ohta, H. Chem. Lett. 1989, 1953-1956. For studies on isolated thiiranium salts, see:
-
(1989)
Chem. Lett
, pp. 1953-1956
-
-
Okuma, K.1
Koike, T.2
Yamamoto, S.3
Yonekura, K.4
Ohta, H.5
-
39
-
-
2142715123
-
-
(g) Owsley, D. C.; Helmkamp, G. K.; Spurlock, S. N. J. Am. Chem. Soc. 1969, 91, 3606-3609.
-
(1969)
J. Am. Chem. Soc
, vol.91
, pp. 3606-3609
-
-
Owsley, D.C.1
Helmkamp, G.K.2
Spurlock, S.N.3
-
41
-
-
0033611941
-
-
(i) Fachini, M.; Lucchini, V.; Modena, G.; Pasi, M.; Pasquato, L. J. Am. Chem. Soc. 1999, 121, 3944-3950.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 3944-3950
-
-
Fachini, M.1
Lucchini, V.2
Modena, G.3
Pasi, M.4
Pasquato, L.5
-
42
-
-
0001059675
-
-
(j) Lucchini, V.; Modena, G.; Pasi, M.; Pasquato, L. J. Org. Chem. 1997, 62, 7018-7020.
-
(1997)
J. Org. Chem
, vol.62
, pp. 7018-7020
-
-
Lucchini, V.1
Modena, G.2
Pasi, M.3
Pasquato, L.4
-
43
-
-
37049076779
-
-
(k) Lucchini, V.; Modena, G.; Pasquato, L. J. Chem. Soc., Chem. Commun. 1994, 1565-1566.
-
(1994)
J. Chem. Soc., Chem. Commun
, pp. 1565-1566
-
-
Lucchini, V.1
Modena, G.2
Pasquato, L.3
-
47
-
-
70149087140
-
-
Toshimitsu, A.; Hayashi, G.; Terao, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1986, 343-347. (e) Toshimitsu, A.; Ito, M.; Uemura, S. J. Chem. Soc., Chem. Commun. 1989, 530-531.
-
(d) Toshimitsu, A.; Hayashi, G.; Terao, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1986, 343-347. (e) Toshimitsu, A.; Ito, M.; Uemura, S. J. Chem. Soc., Chem. Commun. 1989, 530-531.
-
-
-
-
48
-
-
0029931981
-
-
(f) Toshimitsu, A.; Nakano, K.; Mukai, T.; Tamao, K. J. Am. Chem. Soc. 1996, 118, 2756-2757.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 2756-2757
-
-
Toshimitsu, A.1
Nakano, K.2
Mukai, T.3
Tamao, K.4
-
50
-
-
0032522190
-
-
(h) Wirth, T.; Fragale, G.; Spichty, M. J. Am. Chem. Soc. 1998, 120, 3376-3381.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 3376-3381
-
-
Wirth, T.1
Fragale, G.2
Spichty, M.3
-
51
-
-
0036500138
-
-
(i) Uehlin, L.; Fragale, G.; Wirth, T. Chem. Eur. J. 2002, 8, 1125-1133.
-
(2002)
Chem. Eur. J
, vol.8
, pp. 1125-1133
-
-
Uehlin, L.1
Fragale, G.2
Wirth, T.3
-
52
-
-
70149109211
-
-
Lucchini and co-workers have shown that chiral, nonracemic thiiranium ions generated in situ by sulfenium ion transfer can be trapped at low temperature with good enantioselectivity; see ref 7k
-
Lucchini and co-workers have shown that chiral, nonracemic thiiranium ions generated in situ by sulfenium ion transfer can be trapped at low temperature with good enantioselectivity; see ref 7k.
-
-
-
-
53
-
-
0035945990
-
-
Gruttadauria, M.; Lo Meo, P.; Noto, R. Tetrahedron 2001, 57, 1819-1826.
-
(2001)
Tetrahedron
, vol.57
, pp. 1819-1826
-
-
Gruttadauria, M.1
Lo Meo, P.2
Noto, R.3
-
55
-
-
0001539371
-
-
(b) Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697-1705.
-
(1978)
J. Org. Chem
, vol.43
, pp. 1697-1705
-
-
Reich, H.J.1
Wollowitz, S.2
Trend, J.E.3
Chow, F.4
Wendelborn, D.F.5
-
56
-
-
0032970204
-
-
Sølling, T. I.; Wild, S. B.; Radom, L. Chem. Eur. J. 1999, 5, 509-514.
-
(1999)
Chem. Eur. J
, vol.5
, pp. 509-514
-
-
Sølling, T.I.1
Wild, S.B.2
Radom, L.3
-
57
-
-
0031321667
-
-
(a) Borodkin, G.; Chernyak, E. I.; Shakirov, M. M.; Shubin, V. G. Russ. J. Org. Chem. 1997, 33, 418-419.
-
(1997)
Russ. J. Org. Chem
, vol.33
, pp. 418-419
-
-
Borodkin, G.1
Chernyak, E.I.2
Shakirov, M.M.3
Shubin, V.G.4
-
58
-
-
27844586550
-
-
(b) Borodkin, G.; Chernyak, E. I.; Shakirov, M. M.; Shubin, V. G. Russ. J. Org. Chem. 1998, 34, 1563-1568.
-
(1998)
Russ. J. Org. Chem
, vol.34
, pp. 1563-1568
-
-
Borodkin, G.1
Chernyak, E.I.2
Shakirov, M.M.3
Shubin, V.G.4
-
59
-
-
84869620820
-
-
The thiiranium substrate scope was limited to those compounds that could be prepared cleanly and differentiated from each other by 1H NMR analysis if present in a mixture. The S-Ph analogues of thiiranium ions 5 and 6 were unstable at the temperatures required to perform our investigations. Thiiranium analogues of cyclohexyl seleniranium ions 9 and 10 have been reported in the literature but are not stable above-40 °C
-
The thiiranium substrate scope was limited to those compounds that could be prepared cleanly and differentiated from each other by 1H NMR analysis if present in a mixture. The S-Ph analogues of thiiranium ions 5 and 6 were unstable at the temperatures required to perform our investigations. Thiiranium analogues of cyclohexyl seleniranium ions 9 and 10 have been reported in the literature but are not stable above-40 °C.
-
-
-
-
60
-
-
33947295730
-
-
The relative thermodynamic ground-state energies of seleniranium ions 9 and 13 correspond nicely to the expected relative energies for strained cis-bicyclo[ 4.1.0]heptane and cis-bicyclo[6.1.0]nonane, respectively. Chang, S.-J.; McNally, D.; Shary-Tehrany, S.; Hickey, J.; Boyd, R. H. J. Am. Chem. Soc. 1970, 92, 3109-3118.
-
The relative thermodynamic ground-state energies of seleniranium ions 9 and 13 correspond nicely to the expected relative energies for strained cis-bicyclo[ 4.1.0]heptane and cis-bicyclo[6.1.0]nonane, respectively. Chang, S.-J.; McNally, D.; Shary-Tehrany, S.; Hickey, J.; Boyd, R. H. J. Am. Chem. Soc. 1970, 92, 3109-3118.
-
-
-
-
61
-
-
0033595531
-
-
Wang, X.; Houk, K. N.; Spichty, M.; Wirth, T. J. Am. Chem. Soc. 1999, 121, 8567-8576.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 8567-8576
-
-
Wang, X.1
Houk, K.N.2
Spichty, M.3
Wirth, T.4
|