-
2
-
-
0032527724
-
-
Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844-6845.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 6844-6845
-
-
Jeong, J.U.1
Tao, B.2
Sagasser, I.3
Henniges, H.4
Sharpless, K.B.5
-
3
-
-
0035911045
-
-
Aggarwal, V. K.; Stenson, R. A.; Jones, R. V. H.; Fieldhouse, R.; Blacker, J. Tetrahedron Lett. 2001, 42, 1587-1589.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 1587-1589
-
-
Aggarwal, V.K.1
Stenson, R.A.2
Jones, R.V.H.3
Fieldhouse, R.4
Blacker, J.5
-
4
-
-
4544268904
-
-
(a) Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952-3954.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3952-3954
-
-
Kim, S.K.1
Jacobsen, E.N.2
-
5
-
-
8744264856
-
-
(b) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 3973-3975.
-
(2004)
Org. Lett.
, vol.6
, pp. 3973-3975
-
-
Bartoli, G.1
Bosco, M.2
Carlone, A.3
Locatelli, M.4
Melchiorre, P.5
Sambri, L.6
-
6
-
-
0000673216
-
-
Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
-
Also, for reviews on enantioselective aziridination, see: (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (d) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
, pp. 607-618
-
-
Jacobsen, E.N.1
-
7
-
-
0042881024
-
-
Also, for reviews on enantioselective aziridination, see: (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (d) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
-
(2003)
Chem. Rev.
, vol.103
, pp. 2905-2919
-
-
Müller, P.1
Fruit, C.2
-
10
-
-
9444294970
-
-
Hodgson, D. M.; Reynolds, N. J.; Coote, S. J. Org. Lett. 2004, 6, 4187-4189.
-
(2004)
Org. Lett.
, vol.6
, pp. 4187-4189
-
-
Hodgson, D.M.1
Reynolds, N.J.2
Coote, S.J.3
-
11
-
-
0037190868
-
-
Hodgson, D. M.; Reynolds, N. J.; Coote, S. J. Tetrahedron Lett. 2002, 43, 7895-7897.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7895-7897
-
-
Hodgson, D.M.1
Reynolds, N.J.2
Coote, S.J.3
-
13
-
-
0037023469
-
-
(b) Aggarwal, V. K.; Alonso, E.; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335-2344.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 2335-2344
-
-
Aggarwal, V.K.1
Alonso, E.2
Ferrara, M.3
Spey, S.E.4
-
14
-
-
84982383124
-
-
(a) Quast, H.; Vélez, C. A. W. Angew. Chem., Int. Ed. Engl. 1974, 13, 342-343.
-
(1974)
Angew. Chem., Int. Ed. Engl.
, vol.13
, pp. 342-343
-
-
Quast, H.1
Vélez, C.A.W.2
-
15
-
-
0038717316
-
-
For a recent example, see: (b) Hayes, J. F.; Prévost, N.; Prokexfo, I.; Shipman, M.; Slawin, A. M. Z.; Twin, H. Chem. Commun. 2003, 1344-1345.
-
(2003)
Chem. Commun.
, pp. 1344-1345
-
-
Hayes, J.F.1
Prévost, N.2
Prokexfo, I.3
Shipman, M.4
Slawin, A.M.Z.5
Twin, H.6
-
16
-
-
0028353637
-
-
Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M. J. Org. Chem. 1994, 59, 276-277.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 276-277
-
-
Beak, P.1
Wu, S.2
Yum, E.K.3
Jun, Y.M.4
-
17
-
-
18244376456
-
-
note
-
10 80%) of a 1.7:1 trans/cis mixture of α,β-aziridinylsilanes.
-
-
-
-
18
-
-
18244369598
-
-
note
-
3SiCl (3 equiv) in THF, the N-Boc aziridine of 1-hexene could be successfully silylated at -78°C (silylation was unsuccessful at 0°C) in 1 h (69%, >99% trans:cis), but this could not be usefully extended to other electrophiles.
-
-
-
-
19
-
-
0000822788
-
-
Sun, P.; Weinreb, S. M.; Shang, M. J. J. Org. Chem. 1997, 62, 8604-8608.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 8604-8608
-
-
Sun, P.1
Weinreb, S.M.2
Shang, M.J.3
-
20
-
-
8144227335
-
-
Hodgson, D. M.; Stefane, B.; Miles, T. J.; Witherington, J. Chem. Commun. 2004, 2234-2235.
-
(2004)
Chem. Commun.
, pp. 2234-2235
-
-
Hodgson, D.M.1
Stefane, B.2
Miles, T.J.3
Witherington, J.4
-
21
-
-
0005498666
-
-
Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783-786.
-
(1999)
Org. Lett.
, vol.1
, pp. 783-786
-
-
Gontcharov, A.V.1
Liu, H.2
Sharpless, K.B.3
-
22
-
-
18244370370
-
-
note
-
HH = 8 Hz for related N-Ts α,β-aziridinylsilanes.
-
-
-
-
23
-
-
37049067518
-
-
Yanagisawa, A.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1994, 2103-2104.
-
(1994)
J. Chem. Soc., Chem. Commun.
, pp. 2103-2104
-
-
Yanagisawa, A.1
Yasue, K.2
Yamamoto, H.3
-
25
-
-
3242681337
-
-
Hodgson, D. M.; Chung, Y. K.; Paris, J. M. J. Am. Chem. Soc. 2004, 126, 8664-8665.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8664-8665
-
-
Hodgson, D.M.1
Chung, Y.K.2
Paris, J.M.3
-
26
-
-
18244399964
-
-
note
-
1H NMR analysis of the crude reaction mixtures showed substantial byproduct formation.
-
-
-
-
27
-
-
18244375981
-
-
note
-
2O or EtOAc) gave the α,β-aziridinylsilane.
-
-
-
-
28
-
-
18244402034
-
-
note
-
Determined by specific rotation comparison of the starting enantioenriched (S)-1-(tert-butylsulfonyl)-2-decylaziridine and a sample prepared by TBAF-mediated desilylation of the enantioenriched α,β-aziridinylsilane (see Supporting Information).
-
-
-
-
29
-
-
33847805576
-
-
Reference 7
-
For examples of related observations between LTMP and 2,3-disubstitued epoxides, see: (a) Yasuda, A.; Tanaka, S.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6513-6514. (b) Reference 7.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 6513-6514
-
-
Yasuda, A.1
Tanaka, S.2
Oshima, K.3
Yamamoto, H.4
Nozaki, H.5
-
31
-
-
0001092074
-
-
(b) Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4158.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 4156-4158
-
-
Taylor, S.L.1
Lee, D.Y.2
Martin, J.C.3
-
32
-
-
18244396454
-
-
note
-
3SnCl.
-
-
-
-
33
-
-
18244379140
-
-
note
-
2 resulted in contamination with undesired tin byproducts.
-
-
-
-
34
-
-
18244390817
-
-
note
-
3OD after 5 min gave a lower yield of aziridine 6.
-
-
-
-
35
-
-
0001318042
-
-
Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
-
(1996)
Chem. Rev.
, vol.96
, pp. 3303-3325
-
-
Satoh, T.1
-
36
-
-
18244403373
-
-
note
-
We suspect that the modest yields in these cases are due to the other diastereomer being formed competitively, but undergoing degradation via N- to O- Bus migration.
-
-
-
-
37
-
-
0001365666
-
-
Frye, L. L.; Sullivan, E. L.; Cusack, K. P.; Funaro, J. M. J. Org. Chem. 1992, 57, 697-701.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 697-701
-
-
Frye, L.L.1
Sullivan, E.L.2
Cusack, K.P.3
Funaro, J.M.4
-
38
-
-
18244385848
-
-
CCDC 259770 available at http://www.ccdc.cam.ac.uk.
-
-
-
-
39
-
-
37049074033
-
-
(a) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
-
(1991)
J. Chem. Soc., Perkin Trans. 1
, pp. 897-908
-
-
Ashwell, M.1
Clegg, W.2
Jackson, R.F.W.3
-
40
-
-
0141507051
-
-
(b) Jackson, R. F. W.; Dunn, S. F. C. McCamley, A.; Clegg, W. Org. Biomol. Chem. 2003, 1, 2527-2530.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 2527-2530
-
-
Jackson, R.F.W.1
Dunn, S.F.C.2
McCamley, A.3
Clegg, W.4
-
41
-
-
18244405156
-
-
note
-
Attempted trapping with other electrophiles, such as allyl bromide, BnBr, BuOTf, and MeI, has so far been unsuccessful.
-
-
-
-
44
-
-
18244395178
-
-
note
-
2, or Florisil for the aziridinyl aldehyde in entry 8) gave the substituted aziridine.
-
-
-
-
48
-
-
0242558380
-
-
(b) Vedejs, E.; Prasad, A. S. B.; Kendall, J. T.; Russel, J. S. Tetrahedron 2003, 59, 9849-9857.
-
(2003)
Tetrahedron
, vol.59
, pp. 9849-9857
-
-
Vedejs, E.1
Prasad, A.S.B.2
Kendall, J.T.3
Russel, J.S.4
|