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Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5859-5862

Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-Aryl-N-tosylazetidines and aziridines by alcohols

(3) Ghorai, Manas K a Das, Kalpataru a Shukla, Dipti a

a INDIAN INSTITUTE OF TECHNOLOGY KANPUR (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; ALCOHOLS; ENANTIOMERS; ETHERS; REGIOSELECTIVITY; RING OPENING POLYMERIZATION;

AZETIDINES; LEWIS ACID; TOSYLAZETIDINES;

AMINES;

ALCOHOL DERIVATIVE; AZETIDINE DERIVATIVE; AZIRIDINE DERIVATIVE; LEWIS ACID;

ARTICLE; ENANTIOMER; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 34547126202 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0703294 Document Type: Article

Times cited : (63)

References (58)

1
- 1542375289
- For ring opening of aziridines: a, and references cited therein
- For ring opening of aziridines: (a) Hu, X. E. Tetrahedron 2004, 60, 2701-2743 and references cited therein.
- (2004) Tetrahedron , vol.60 , pp. 2701-2743
- Hu, X.E.¹

2
- 23944498051
- (b) Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509-3512.
- (2005) Org. Lett , vol.7 , pp. 3509-3512
- Minakata, S.¹ Okada, Y.² Oderaotoshi, Y.³ Komatsu, M.⁴

3
- 27744573140
- (c) Ding, C. H.; Dai, L. X.; Hou, X. L. Tetrahedron 2005, 61, 9586-9593.
- (2005) Tetrahedron , vol.61 , pp. 9586-9593
- Ding, C.H.¹ Dai, L.X.² Hou, X.L.³

4
- 16444370558
- (d) Pineschi, M.; Bertolini, F.; Haak, R. M.; Crotti, P.; Macchia, F. Chem. Commun. 2005, 1426-1428.
- (2005) Chem. Commun , pp. 1426-1428
- Pineschi, M.¹ Bertolini, F.² Haak, R.M.³ Crotti, P.⁴ Macchia, F.⁵

5
- 33749039462
- (e) Minakata, S.; Hotta, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2006, 71, 7471-7472.
- (2006) J. Org. Chem , vol.71 , pp. 7471-7472
- Minakata, S.¹ Hotta, T.² Oderaotoshi, Y.³ Komatsu, M.⁴

6
- 33646560979
- (f) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312-6313.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 6312-6313
- Fukuta, Y.¹ Mita, T.² Fukuda, N.³ Kanai, M.⁴ Shibasaki, M.⁵

7
- 0001108771
- Three- and Four-Membered Rings, With All Fused Systems Containing Three- and Four-Membered Rings
- Padwa, A, Ed, Elsevier: Oxford, Chapter 1.21
- (g) De Kimpe, N. Three- and Four-Membered Rings, With All Fused Systems Containing Three- and Four-Membered Rings. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Oxford 1996; Vol. 1, Chapter 1.21.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.1
- De Kimpe, N.¹

8
- 0028240601
- For ring opening of azetidines: h
- For ring opening of azetidines: (h) Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1994, 50, 5775-5782.
- (1994) Tetrahedron , vol.50 , pp. 5775-5782
- Almena, J.¹ Foubelo, F.² Yus, M.³

9
- 0142106416
- (i) Akiyama, T.; Daidouji, K.; Fuchibe, K. Org. Lett. 2003, 5, 3691-3693.
- (2003) Org. Lett , vol.5 , pp. 3691-3693
- Akiyama, T.¹ Daidouji, K.² Fuchibe, K.³

10
- 30144437267
- (j) Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 7, 5861-5864.
- (2005) Org. Lett , vol.7 , pp. 5861-5864
- Vargas-Sanchez, M.¹ Couty, F.² Evano, G.³ Prim, D.⁴ Marrot, J.⁵

11
- 33344470460
- (k) Domostoj, M.; Ungureanu, I.; Schoenfelder, A.; Klotz, P.; Mann, A. Tetrahedron Lett. 2006, 47, 2205-2208.
- (2006) Tetrahedron Lett , vol.47 , pp. 2205-2208
- Domostoj, M.¹ Ungureanu, I.² Schoenfelder, A.³ Klotz, P.⁴ Mann, A.⁵

12
- 33646452114
- (l) Van Brabandt, W.; Van Landeghem, R.; De Kimpe, N. Org. Lett. 2006, 8, 1105-1108.
- (2006) Org. Lett , vol.8 , pp. 1105-1108
- Van Brabandt, W.¹ Van Landeghem, R.² De Kimpe, N.³

13
- 0028935256
- (m) Golding, P; Millar, R. W.; Paul, N. C.; Richards, D. H. Tetrahedron 1995, 51, 5073-5082.
- (1995) Tetrahedron , vol.51 , pp. 5073-5082
- Golding, P.¹ Millar, R.W.² Paul, N.C.³ Richards, D.H.⁴

14
- 22244445827
- (n) Vanecko, J. A.; West, F. G. Org. Lett. 2005, 7, 2949-2952.
- (2005) Org. Lett , vol.7 , pp. 2949-2952
- Vanecko, J.A.¹ West, F.G.²

15
- 10044237878
- For cycloaddition of aziridines: a
- For cycloaddition of aziridines: (a) Concellón, J. M.; Riego, E.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2004, 6, 4499-4501.
- (2004) Org. Lett , vol.6 , pp. 4499-4501
- Concellón, J.M.¹ Riego, E.² Suárez, J.R.³ García-Granda, S.⁴ Díaz, M.R.⁵

16
- 29444435219
- (b) Zhu, W.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 5545-5548.
- (2005) Org. Lett , vol.7 , pp. 5545-5548
- Zhu, W.¹ Cai, G.² Ma, D.³

17
- 33745195464
- and references cited therein
- (c) Ghorai, M. K.; Ghosh, K.; Das, K. Tetrahedron Lett. 2006, 47, 5399-5403 and references cited therein.
- (2006) Tetrahedron Lett , vol.47 , pp. 5399-5403
- Ghorai, M.K.¹ Ghosh, K.² Das, K.³

18
- 0035822109
- For cycloaddition of azetidines: d
- For cycloaddition of azetidines: (d) Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Chem. Commun. 2001, 958-959.
- (2001) Chem. Commun , pp. 958-959
- Ungureanu, I.¹ Klotz, P.² Schoenfelder, A.³ Mann, A.⁴

19
- 0035959482
- (e) Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Tetrahedron Lett. 2001, 42, 6087-6091.
- (2001) Tetrahedron Lett , vol.42 , pp. 6087-6091
- Ungureanu, I.¹ Klotz, P.² Schoenfelder, A.³ Mann, A.⁴

20
- 12344319209
- (f) Prasad, B. A. B.; Bisai, A.; Singh, V. K. Org. Lett. 2004, 6, 4829-4831.
- (2004) Org. Lett , vol.6 , pp. 4829-4831
- Prasad, B.A.B.¹ Bisai, A.² Singh, V.K.³

21
- 28444460250
- (g) Yadav, V. K.; Sriramurthy, V. J. Am. Chem. Soc. 2005, 127, 16366-16367.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 16366-16367
- Yadav, V.K.¹ Sriramurthy, V.²

22
- 0242513268
- (h) Baeg, J. O.; Bensimon, C.; Alper, H. J. Org. Chem. 1995, 60, 253-256.
- (1995) J. Org. Chem , vol.60 , pp. 253-256
- Baeg, J.O.¹ Bensimon, C.² Alper, H.³

23
- 0029049859
- (i) Baeg, J. O.; Bensimon, C.; Alper, H. Ibid. 1995, 60, 3092-3095.
- (1995) J. Org. Chem , vol.60 , pp. 3092-3095
- Baeg, J.O.¹ Bensimon, C.² Alper, H.³

24
- 0033601329
- and the references cited therein
- Alcaide, B.; Almendros, P.; Aragoncillo, C.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596-9604 and the references cited therein.
- (1999) J. Org. Chem , vol.64 , pp. 9596-9604
- Alcaide, B.¹ Almendros, P.² Aragoncillo, C.³ Salgado, N.R.⁴

25
- 18844399915
- (a) Ghorai, M. K.; Das, K.; Kumar, A.; Ghosh, K. Tetrahedron Lett. 2005, 46, 4103-4106.
- (2005) Tetrahedron Lett , vol.46 , pp. 4103-4106
- Ghorai, M.K.¹ Das, K.² Kumar, A.³ Ghosh, K.⁴

26
- 33745222531
- (b) Ghorai, M. K.; Das, K.; Kumar, A.; Das, A. Tetrahedron Lett. 2006, 47, 5393-5397.
- (2006) Tetrahedron Lett , vol.47 , pp. 5393-5397
- Ghorai, M.K.¹ Das, K.² Kumar, A.³ Das, A.⁴

27
- 33745195464
- (c) Ghorai, M. K.; Ghosh, K.; Das, K. Tetrahedron Lett. 2006, 47, 5399-5403.
- (2006) Tetrahedron Lett , vol.47 , pp. 5399-5403
- Ghorai, M.K.¹ Ghosh, K.² Das, K.³

28
- 34547094404
- Unpublished results
- (a) Ghorai, M. K.; Kumar, A.; Das, K. Unpublished results.
- Ghorai, M.K.¹ Kumar, A.² Das, K.³

29
- 34248683615
- doi: 10.1016/ j.tetlet.2007.04.097
- (b) Ghorai, M. K.; Das, K.; Kumar, A. Tetrahedron Lett. 2007, doi: 10.1016/ j.tetlet.2007.04.097.
- (2007) Tetrahedron Lett
- Ghorai, M.K.¹ Das, K.² Kumar, A.³

30
- 34047103319
- (c) Ghorai, M. K.; Ghosh, K. Tetrahedron Lett. 2007, 48, 3191-3195.
- (2007) Tetrahedron Lett , vol.48 , pp. 3191-3195
- Ghorai, M.K.¹ Ghosh, K.²

31
- 0023860773
- and references cited therein
- Robertson, D. W.; Jones, N. D.; Swartzendruber, J. K.; Yang, K. S.; Wong, D. T. J. Med. Chem. 1988, 31, 185-189 and references cited therein.
- (1988) J. Med. Chem , vol.31 , pp. 185-189
- Robertson, D.W.¹ Jones, N.D.² Swartzendruber, J.K.³ Yang, K.S.⁴ Wong, D.T.⁵

32
- 0842287699
- Silver, H. Int. Clin. Psychopharm. 2003, 18, 305-313.
- (2003) Int. Clin. Psychopharm , vol.18 , pp. 305-313
- Silver, H.¹

33
- 0029029578
- Wong, D. T.; Bymaster, F. P.; Engleman, E. A. Life Sci. 1995, 57, 411-441.
- (1995) Life Sci , vol.57 , pp. 411-441
- Wong, D.T.¹ Bymaster, F.P.² Engleman, E.A.³

34
- 0021320065
- Chouinard, G.; Annable, L.; Bradwejn, J. Psychopharmacology 1984, 83, 126-128.
- (1984) Psychopharmacology , vol.83 , pp. 126-128
- Chouinard, G.¹ Annable, L.² Bradwejn, J.³

35
- 23044484402
- (a) Li, Y.; Li, Z.; Li, F.; Wang, Q.; Tao, F. Org. Bimol. Chem. 2005, 3, 2513-2518.
- (2005) Org. Bimol. Chem , vol.3 , pp. 2513-2518
- Li, Y.¹ Li, Z.² Li, F.³ Wang, Q.⁴ Tao, F.⁵

36
- 0037040674
- (b) Watanabe, M.; Murata, K.; Ikariya, T. J. Org. Chem. 2002, 67, 1712-1715.
- (2002) J. Org. Chem , vol.67 , pp. 1712-1715
- Watanabe, M.¹ Murata, K.² Ikariya, T.³

37
- 0037037886
- (c) O'Brien, P.; Phillips, D. W.; Towers, T. D. Tetrahedron Lett. 2002, 43, 7333-7335.
- (2002) Tetrahedron Lett , vol.43 , pp. 7333-7335
- O'Brien, P.¹ Phillips, D.W.² Towers, T.D.³

38
- 9944253219
- (d) Kumar, P.; Upadhyay, R. K.; Pandey, R. K. Tetrahedron: Asymmetry 2004, 15, 3955-3959.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3955-3959
- Kumar, P.¹ Upadhyay, R.K.² Pandey, R.K.³

39
- 0037145055
- (e) Kamal, A.; Khanna, G. B. R.; Ramu, R. Tetrahedron: Asymmetry 2002, 13, 2039-2051.
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 2039-2051
- Kamal, A.¹ Khanna, G.B.R.² Ramu, R.³

40
- 13544276556
- (f) Bhandari, K.; Srivastava, S.; Shanker, G.; Nath, C. Bioorg. Med. Chem. 2005, 13, 1739-1747.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 1739-1747
- Bhandari, K.¹ Srivastava, S.² Shanker, G.³ Nath, C.⁴

41
- 0035820047
- and references cited there in. 2001
- Boger, D. L.; Kim, S. H.; Mori, Y.; Weng, J. H.; Rogel, O.; Castle, S. L.; McAtee, J. J. J. Am. Chem. Soc. 2001, 123, 1862-1871 and references cited there in.
- (1862) J. Am. Chem. Soc , vol.123
- Boger, D.L.¹ Kim, S.H.² Mori, Y.³ Weng, J.H.⁴ Rogel, O.⁵ Castle, S.L.⁶ McAtee, J.J.⁷

42
- 0027517214
- Ho, M.; Chung, J. K. K.; Tang, N. Tetrahedron Lett. 1993, 34, 6513-6516.
- (1993) Tetrahedron Lett , vol.34 , pp. 6513-6516
- Ho, M.¹ Chung, J.K.K.² Tang, N.³

43
- 84985057438
- (a) Bucholz, B.; Stamm, H. Isr. J. Chem. 1986, 27, 17-23.
- (1986) Isr. J. Chem , vol.27 , pp. 17-23
- Bucholz, B.¹ Stamm, H.²

44
- 0030790051
- (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253-5256.
- (1997) Tetrahedron Lett , vol.38 , pp. 5253-5256
- Maligres, P.E.¹ See, M.M.² Askin, D.³ Reider, P.J.⁴

45
- 0037100090
- (c) Yadav, J. S.; Reddy, B. V. S.; Balanarsaiah, E.; Raghavendra, S. Tetrahedron Lett. 2002, 43, 5105-5107.
- (2002) Tetrahedron Lett , vol.43 , pp. 5105-5107
- Yadav, J.S.¹ Reddy, B.V.S.² Balanarsaiah, E.³ Raghavendra, S.⁴

46
- 0037008918
- (d) Prasad, B. A. B.; Sanghi, R.; Singh, V, K. Tetrahedron 2002, 58, 7355-7363.
- (2002) Tetrahedron , vol.58 , pp. 7355-7363
- Prasad, B.A.B.¹ Sanghi, R.² Singh, V.K.³

47
- 8144227335
- (a) 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

48
- 0030768283
- (b) Furth, P. S.; Reitman, M. S.; Gentles, R.; Cook, A. F. Tetrahedron Lett. 1997, 38, 6643-6646.
- (1997) Tetrahedron Lett , vol.38 , pp. 6643-6646
- Furth, P.S.¹ Reitman, M.S.² Gentles, R.³ Cook, A.F.⁴

49
- 2542514849
- (c) Sott, R.; Granander, J.; Hilmersson, G. J. Am. Chem. Soc. 2004, 126, 6798-6805.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 6798-6805
- Sott, R.¹ Granander, J.² Hilmersson, G.³

50
- 0346218217
- (d) Ramírez, A.; Lobkovsky, E.; Collum, D. B.; J. Am. Chem. Soc. 2003, 125, 15376-15387.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 15376-15387
- Ramírez, A.¹ Lobkovsky, E.² Collum, D.B.³

51
- 0028356205
- (e) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586.
- (1994) Tetrahedron Lett , vol.35 , pp. 4585-4586
- Okuda, M.¹ Tomioka, K.²

52
- 0027260798
- (e) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1993, 4, 1603-1606.
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1603-1606
- Inoue, I.¹ Shindo, M.² Koga, K.³ Tomioka, K.⁴

53
- 9944231418
- (f) Periasamy, M.; Seenivasaperumal, M.; Rao, V. D. Tetrahedron: Asymmetry 2004, 15, 3847-3852.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3847-3852
- Periasamy, M.¹ Seenivasaperumal, M.² Rao, V.D.³

54
- 15944417864
- (g) Aravind, A.; Mohanty, S. K.; Pratap, T. V.; Baskaran, S. Tetrahedron Lett. 2005, 46, 2965-2968.
- (2005) Tetrahedron Lett , vol.46 , pp. 2965-2968
- Aravind, A.¹ Mohanty, S.K.² Pratap, T.V.³ Baskaran, S.⁴

55
- 33847618382
- Ghorai, M. K.; Das, K.; Kumar, A. Tetrahedron Lett. 2007, 48, 2471-2475.
- (2007) Tetrahedron Lett , vol.48 , pp. 2471-2475
- Ghorai, M.K.¹ Das, K.² Kumar, A.³

56
- 34547111096
- Details are provided in the Supporting Information
- Details are provided in the Supporting Information.

57
- 34547096788
- The absolute configuration of 1,3-amino ether prepared from (S)-mandelic acid and that obtained from (S)-2-phenyl-N- tosylazetidine is the same. Details of the preparation of authentic compound are provided in the Supporting Information.
- The absolute configuration of 1,3-amino ether prepared from (S)-mandelic acid and that obtained from (S)-2-phenyl-N- tosylazetidine is the same. Details of the preparation of authentic compound are provided in the Supporting Information.

58
- 34547100804
- The absolute stereochemistry for the major enantiomer of 6a was determined by compairing optical rotation and chiral HPLC analysis of an authentic compound (ee 98%) prepared from (S)-mandelic acid (ee > 99%). The absolute configuration of 1,2-amino ether prepared from (S)-mandelic acid and that obtained from (R)-2-phenyl-N- tosylaziridine is the same. Details of the preparation of authentic compound for (S)-6a is provided in the Supporting Information.
- The absolute stereochemistry for the major enantiomer of 6a was determined by compairing optical rotation and chiral HPLC analysis of an authentic compound (ee 98%) prepared from (S)-mandelic acid (ee > 99%). The absolute configuration of 1,2-amino ether prepared from (S)-mandelic acid and that obtained from (R)-2-phenyl-N- tosylaziridine is the same. Details of the preparation of authentic compound for (S)-6a is provided in the Supporting Information.

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