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Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 7920-7925

Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry

(2) Pepito, Aurora S a Dittmer, Donald C a

a SYRACUSE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000426838 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo962024n Document Type: Article

Times cited : (19)

References (143)

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45
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46
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- Reaction of alkynes with metalloimines, of titanium-alkyne derivatives with imines, or of propargylamines with aryl bromides via cross-coupling involving tri-n-butyltin hydride and palladium: (o) Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem. Soc., Perkin Trans. 1 1996, 2869-2872. (p) Takai, K.; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1994, 35, 1893-1896. (q) Gao, Y.; Harada, K.; Sato, F. Tetrahedron Lett. 1995, 5913-5916. (r) Corriu, R. J. P.; Bolin, G.; Moreau, J. J. E. Bull. Soc. Chim. Fr. 1993, 130, 273-280.
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47
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- Methylenation reactions (e.g., Wittig): see also ref 8a,d. (s) Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247. (t) Katritzky, A. R.; Hong, Q.; Chen, J.; Yang, Z.; Belyakov, S. A. An. Quim. Int. Ed. 1996, 92, 138-140; Chem. Abstr. 1996, 125, 275770. (u) Albeck, A.; Persky, R. J. Org. Chem. 1994, 59, 653-657. (v) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1991, 56, 1027-1036. (w) Wei, Z.- Y.; Knaus, E. E. Synthesis 1994, 1463-1466.
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48
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49
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- (1996) Chem. Abstr. , vol.125 , pp. 275770

50
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- (1994) J. Org. Chem. , vol.59 , pp. 653-657
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51
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52
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53
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- Loreto, M.A.¹ Tardella, P.A.² Tofani, D.³

54
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- From aziridines: (x) Loreto, M. A.; Tardella, P. A.; Tofani, D. Tetrahedron Lett. 1995, 36, 8295-8298. (y) DeKimpe, N.; Jolie, R.; DeSmaele, D. J. Chem. Soc., Chem. Commun. 1994, 1221-1222. (z) da Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602-2615.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 1221-1222
- DeKimpe, N.¹ Jolie, R.² DeSmaele, D.³

55
- 17044385237
- From aziridines: (x) Loreto, M. A.; Tardella, P. A.; Tofani, D. Tetrahedron Lett. 1995, 36, 8295-8298. (y) DeKimpe, N.; Jolie, R.; DeSmaele, D. J. Chem. Soc., Chem. Commun. 1994, 1221-1222. (z) da Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602-2615.
- (1993) Helv. Chim. Acta , vol.76 , pp. 2602-2615
- Da Zhang, Z.¹ Scheffold, R.²

56
- 0000059289
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1997) J. Org. Chem. , vol.62 , pp. 2288-2291
- Overman, L.E.¹ Zipp, G.G.²

57
- 0030501645
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1996) Chem. Lett. , pp. 385-386
- Honda, K.¹ Tabuchi, M.² Inoue, S.³

58
- 0029145169
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6725-6728
- Nishibayashi, Y.¹ Srivastava, S.K.² Ohe, K.³ Uemura, S.⁴

59
- 0000332081
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1996) J. Org. Chem. , vol.61 , pp. 2932-2933
- Kurose, N.¹ Takahashi, T.² Koizumi, T.³

60
- 0013621887
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2791-2796
- Ichikawa, Y.¹ Tsuboi, K.² Isobe, M.³

61
- 0029926328
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1996) Tetrahedron Lett. , vol.37 , pp. 2573-2576
- Imogai, H.¹ Petit, Y.² Larcheveque, M.³

62
- 0001215094
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1986) J. Org. Chem. , vol.51 , pp. 5243-5252
- Shea, R.G.¹ Fitzner, J.N.² Fankhauser, J.E.³ Spaltenstein, A.⁴ Carpino, P.A.⁵ Peevey, R.M.⁶ Pratt, D.V.⁷ Tenge, B.J.⁸ Hopkins, P.B.⁹

63
- 33748228466
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
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- Brunko, M.¹ Khuong, T.A.V.² Sharpless, K.B.³

64
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- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 3526-3529
- Whitesell, J.K.¹ Yaser, H.K.²

65
- 0029997340
- Sigmatropic rearrangements: (aa) Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291. (bb) Honda, K.; Tabuchi, M.; Inoue, S. Chem. Lett. 1996, 385-386. (cc) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725-6728. (dd) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933. fee) Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791-2796. (ff) Imogai, H.; Petit, Y.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576. (gg) Shea, R. G.; Fitzner, J. N.; Fankhauser, J. E.; Spaltenstein, A.; Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 5243-5252. (hh) Brunko, M.; Khuong, T.- A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454- 456. (ii) Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526-3529. (jj) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 1329-1334. (kk) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
- (1996) Synth. Commun. , vol.26 , pp. 1329-1334
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- note
- The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystal- lographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.