-
1
-
-
33748605775
-
-
1) For representative overviews of aziridine chemistry, see: a
-
( 1) For representative overviews of aziridine chemistry, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
-
(1994)
Angew. Chem., Int. Ed. Engl
, vol.33
, pp. 599
-
-
Tanner, D.1
-
5
-
-
0345975526
-
-
For reviews on aziridine ring opening, see: a
-
For reviews on aziridine ring opening, see: (a) Stamm, H. J. Prakt. Chem. 1999, 341, 319.
-
(1999)
J. Prakt. Chem
, vol.341
, pp. 319
-
-
Stamm, H.1
-
7
-
-
1542375289
-
-
(c) Hu, X. E. Tetrahedron 2004, 60, 2701.
-
(2004)
Tetrahedron
, vol.60
, pp. 2701
-
-
Hu, X.E.1
-
8
-
-
0030907093
-
-
For reviews on the preparation of aziridines, see: a
-
For reviews on the preparation of aziridines, see: (a) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 1693
-
-
Osborn, H.M.I.1
Sweeney, J.2
-
14
-
-
84890760012
-
-
Evans, P. A, Ed, Wiley-VCH: Weinheim
-
(e) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2006, 379.
-
(2006)
Modern Rhodium-Catalyzed Organic Reactions
, pp. 379
-
-
Espino, C.G.1
Du Bois, J.2
-
15
-
-
33645512284
-
-
(f) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194.
-
(2006)
Acc. Chem. Res
, vol.39
, pp. 194
-
-
Watson, I.D.G.1
Yu, L.2
Yudin, A.K.3
-
16
-
-
33644526230
-
-
(g) Lebel, H.; Leogane, O.; Huard, K.; Lectard, S. Pure Appl. Chem. 2006, 78, 363.
-
(2006)
Pure Appl. Chem
, vol.78
, pp. 363
-
-
Lebel, H.1
Leogane, O.2
Huard, K.3
Lectard, S.4
-
18
-
-
33847804544
-
-
(a) Abramovitch, R. A.; Bailey, T. D.; Takaya, T.; Uma, V. J. Org. Chem. 1974, 39, 340.
-
(1974)
J. Org. Chem
, vol.39
, pp. 340
-
-
Abramovitch, R.A.1
Bailey, T.D.2
Takaya, T.3
Uma, V.4
-
20
-
-
11644312278
-
-
For some representative examples, see: a
-
For some representative examples, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
-
(1994)
J. Am. Chem. Soc
, vol.116
, pp. 2742
-
-
Evans, D.A.1
Faul, M.M.2
Bilodeau, M.T.3
-
21
-
-
0037782375
-
-
(b) Södergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897.
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 6897
-
-
Södergren, M.J.1
Alonso, D.A.2
Bedekar, A.V.3
Andersson, P.G.4
-
23
-
-
1942504284
-
-
(d) Kwong, H.-L.; Liu, D.; Chan, K.-Y.; Lee, C.-S.; Huang, K.-H.; Che, C.-M. Tetrahedron Lett. 2004, 45, 3965.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 3965
-
-
Kwong, H.-L.1
Liu, D.2
Chan, K.-Y.3
Lee, C.-S.4
Huang, K.-H.5
Che, C.-M.6
-
24
-
-
8744317132
-
-
(e) Han, H.; Bae, I.; Yoo, E. J.; Lee, J.; Do, Y.; Chang, S. Org. Lett. 2004, 6, 4109.
-
(2004)
Org. Lett
, vol.6
, pp. 4109
-
-
Han, H.1
Bae, I.2
Yoo, E.J.3
Lee, J.4
Do, Y.5
Chang, S.6
-
25
-
-
20344368322
-
-
(f) Mohr, F.; Binfield, S. A.; Fettinger, J. C.; Vedernikov, A. N. J. Org. Chem. 2005, 70, 4833.
-
(2005)
J. Org. Chem
, vol.70
, pp. 4833
-
-
Mohr, F.1
Binfield, S.A.2
Fettinger, J.C.3
Vedernikov, A.N.4
-
26
-
-
0038660113
-
-
For representative examples, see: a
-
For representative examples, see: (a) Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543.
-
(1996)
Tetrahedron
, vol.52
, pp. 1543
-
-
Müller, P.1
Baud, C.2
Jacquier, Y.3
-
28
-
-
0037069733
-
-
(c) Liang, J.-L.; Yuan, S.-X.; Hong Chan, P. W.; Che, C.-M. Org. Lett. 2002, 4, 4507.
-
(2002)
Org. Lett
, vol.4
, pp. 4507
-
-
Liang, J.-L.1
Yuan, S.-X.2
Hong Chan, P.W.3
Che, C.-M.4
-
29
-
-
4644238043
-
-
(d) Padwa, A.; Flick, A. C.; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377.
-
(2004)
J. Org. Chem
, vol.69
, pp. 6377
-
-
Padwa, A.1
Flick, A.C.2
Leverett, C.A.3
Stengel, T.4
-
31
-
-
27944498664
-
-
(f) Catino, A. J.; Nichols, J. M.; Forslund, R. E.; Doyle, M. P. Org. Lett. 2005, 7, 2787.
-
(2005)
Org. Lett
, vol.7
, pp. 2787
-
-
Catino, A.J.1
Nichols, J.M.2
Forslund, R.E.3
Doyle, M.P.4
-
33
-
-
20644471624
-
-
For recent examples, see: a
-
For recent examples, see: (a) Davies, H. M. L.; Long, M. S. Angew. Chem. Int. Ed. 2005, 44, 3518.
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 3518
-
-
Davies, H.M.L.1
Long, M.S.2
-
34
-
-
33746308969
-
-
(b) Liang, C.; Robert-Peillard, F.; Fruit, C.; Müller, P.; Dodd, R. H.; Dauban, P. Angew. Chem. Int. Ed. 2006, 45, 4641.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 4641
-
-
Liang, C.1
Robert-Peillard, F.2
Fruit, C.3
Müller, P.4
Dodd, R.H.5
Dauban, P.6
-
36
-
-
2342468596
-
-
For recent examples, see: a
-
For recent examples, see: (a) White, R. D.; Keaney, G. F.; Slown, C. D.; Wood, J. L. Org. Lett. 2004, 6, 1123.
-
(2004)
Org. Lett
, vol.6
, pp. 1123
-
-
White, R.D.1
Keaney, G.F.2
Slown, C.D.3
Wood, J.L.4
-
37
-
-
28844471334
-
-
(b) Provoost, O. Y.; Hedley, S. J.; Hazelwood, A. J.; Harrity, J. P. A. Tetrahedron Lett. 2006, 47, 331.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 331
-
-
Provoost, O.Y.1
Hedley, S.J.2
Hazelwood, A.J.3
Harrity, J.P.A.4
-
39
-
-
33747473316
-
-
(d) Kessler, A.; Faure, H.; Petrel, C.; Rognan, D.; Césario, M.; Ruat, M.; Dauban, P.; Dodd, R. H. J. Med. Chem. 2006, 49, 5119.
-
(2006)
J. Med. Chem
, vol.49
, pp. 5119
-
-
Kessler, A.1
Faure, H.2
Petrel, C.3
Rognan, D.4
Césario, M.5
Ruat, M.6
Dauban, P.7
Dodd, R.H.8
-
40
-
-
0141534438
-
-
Rhodium-catalyzed nitrene transfer has found application in total synthesis in the field of C-H amination. Impressive examples of syntheses of highly complex natural products are reported in the following articles: (a) Hinman, A, Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510
-
Rhodium-catalyzed nitrene transfer has found application in total synthesis in the field of C-H amination. Impressive examples of syntheses of highly complex natural products are reported in the following articles: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510.
-
-
-
-
42
-
-
0007448978
-
-
(a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
-
(1993)
J. Am. Chem. Soc
, vol.115
, pp. 5326
-
-
Li, Z.1
Conser, K.R.2
Jacobsen, E.N.3
-
43
-
-
0000303283
-
-
(b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
-
(1993)
J. Am. Chem. Soc
, vol.115
, pp. 5328
-
-
Evans, D.A.1
Faul, M.M.2
Bilodeau, M.T.3
Anderson, B.A.4
Barnes, D.M.5
-
44
-
-
0034718094
-
-
(c) Sanders, C. J.; Gillespie, K. M.; Bell, D.; Scott, P. J. Am. Chem. Soc. 2000, 122, 7132.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 7132
-
-
Sanders, C.J.1
Gillespie, K.M.2
Bell, D.3
Scott, P.4
-
45
-
-
0037123608
-
-
(d) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450.
-
(2002)
J. Org. Chem
, vol.67
, pp. 3450
-
-
Gillespie, K.M.1
Sanders, C.J.2
O'Shaughnessy, P.3
Westmoreland, I.4
Thickitt, C.P.5
Scott, P.6
-
46
-
-
10944252068
-
-
(e) Ryan, D.; McMorn, P.; Bethell, D.; Hutchings, G. Org. Biomol. Chem. 2004, 2, 3566.
-
(2004)
Org. Biomol. Chem
, vol.2
, pp. 3566
-
-
Ryan, D.1
McMorn, P.2
Bethell, D.3
Hutchings, G.4
-
48
-
-
27944451724
-
-
(g) Ma, L.; Du, D.-M.; Xu, J. J. Org. Chem. 2005, 70, 10155.
-
(2005)
J. Org. Chem
, vol.70
, pp. 10155
-
-
Ma, L.1
Du, D.-M.2
Xu, J.3
-
50
-
-
0034720956
-
-
(a) Yu, X. Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233.
-
(2000)
Org. Lett
, vol.2
, pp. 2233
-
-
Yu, X.Q.1
Huang, J.-S.2
Zhou, X.-G.3
Che, C.-M.4
-
52
-
-
0034794306
-
-
(c) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7707
-
-
Dauban, P.1
Sanière, L.2
Tarrade, A.3
Dodd, R.H.4
-
53
-
-
0034835815
-
-
(a) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 6935
-
-
Espino, C.G.1
Wehn, P.M.2
Chow, J.3
Du Bois, J.4
-
54
-
-
0345791433
-
-
(b) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823.
-
(2003)
Org. Lett
, vol.5
, pp. 4823
-
-
Wehn, P.M.1
Lee, J.2
Du Bois, J.3
-
56
-
-
2442704159
-
-
(d) Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Che, C.-M. J. Org. Chem. 2004, 69, 3610.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3610
-
-
Liang, J.-L.1
Yuan, S.-X.2
Huang, J.-S.3
Che, C.-M.4
-
58
-
-
33750476666
-
-
(f) Guthikonda, K.; Wehn, P. M.; Caliando, B. J.; Du Bois, J. Tetrahedron 2006, 62, 11331.
-
(2006)
Tetrahedron
, vol.62
, pp. 11331
-
-
Guthikonda, K.1
Wehn, P.M.2
Caliando, B.J.3
Du Bois, J.4
-
59
-
-
0001458273
-
-
Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481.
-
(2002)
Org. Lett
, vol.4
, pp. 2481
-
-
Duran, F.1
Leman, L.2
Ghini, A.3
Burton, G.4
Dauban, P.5
Dodd, R.H.6
-
60
-
-
0034596449
-
-
Okada, M.; Iwashita, S.; Koizumi, N. Tetrahedron Lett. 2000, 41, 7047.
-
(2000)
Tetrahedron Lett
, vol.41
, pp. 7047
-
-
Okada, M.1
Iwashita, S.2
Koizumi, N.3
-
61
-
-
34247597505
-
-
At this stage of the experimental work, preliminary investigations of the nucleophilic ring opening of aziridine 4a with benzylamine revealed that it occurs without loss of stereochemical information. No trace of the cis-isomer of the aziridine ring-opened product was observed, while the ee of the latter matched the ee of the aziridine 4a. According to subsequent experiments (vide infra) and Du Bois's work see ref. 13f, the reaction is believed to occur by an SN2 process. This result was used to derivatize aziridines 4b-j by reaction with benzylamine in order to determine the enantioselectivity of the asymmetric intramolecular aziridination of sulfamates 2b-j
-
N2 process. This result was used to derivatize aziridines 4b-j by reaction with benzylamine in order to determine the enantioselectivity of the asymmetric intramolecular aziridination of sulfamates 2b-j.
-
-
-
-
62
-
-
0000072415
-
-
(a) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 5889
-
-
Li, Z.1
Quan, R.W.2
Jacobsen, E.N.3
-
63
-
-
0040518632
-
-
(b) Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 8013
-
-
Brandt, P.1
Södergren, M.J.2
Andersson, P.G.3
Norrby, P.-O.4
-
64
-
-
10044280513
-
-
For the diastereoselective catalytic aziridination of acrylate derivatives, see
-
For the diastereoselective catalytic aziridination of acrylate derivatives, see: Di Chenna, P. H.; Robert-Peillard, F.; Dauban, P.; Dodd, R. H. Org. Lett. 2004, 6, 4503.
-
(2004)
Org. Lett
, vol.6
, pp. 4503
-
-
Di Chenna, P.H.1
Robert-Peillard, F.2
Dauban, P.3
Dodd, R.H.4
-
65
-
-
34247557198
-
-
Estéoule, A.; Dodd, R. H.; Dauban, P. unpublished results.
-
Estéoule, A.; Dodd, R. H.; Dauban, P. unpublished results.
-
-
-
-
66
-
-
0037424821
-
-
For a review on cyclic sulfamidates, see
-
For a review on cyclic sulfamidates, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581.
-
(2003)
Tetrahedron
, vol.59
, pp. 2581
-
-
Meléndez, R.E.1
Lubell, W.D.2
-
67
-
-
34247610060
-
-
Collect' data collection software;
-
'Collect' data collection software; Nonius, B. V.; 1999.
-
Nonius, B
, vol.1999
-
-
-
68
-
-
0003473687
-
-
Spek, A. L, Ed, Utrecht University: Utrecht, The Netherlands
-
PLATON, A Multipurpose Crystallographic Tool; Spek, A. L., Ed.; Utrecht University: Utrecht, The Netherlands, 2007.
-
(2007)
PLATON, A Multipurpose Crystallographic Tool
-
-
-
69
-
-
0031059866
-
-
Part A, Carter, C. W. Jr, Sweet, R. M, Eds, Academic Press: New York
-
Otwinowski, Z.; Minor, W. In Methods in Enzymology. Macromolecular Crystallography, Part A, Vol. 276; Carter, C. W. Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997, 307.
-
(1997)
Methods in Enzymology. Macromolecular Crystallography
, vol.276
, pp. 307
-
-
Otwinowski, Z.1
Minor, W.2
|