SCOPUS 정보 검색 플랫폼

Volumn 36, Issue 1, 2007, Pages 82-83

Regio- and stereoselective ring opening of epoxides and aziridines using zirconyl chloride: An efficient approach for the synthesis of β-chlorohydrins and β-chloroamines

(3) Das, Biswanath a Krishnaiah, Maddeboina a Venkateswarlu, Katta a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247184222 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.82 Document Type: Article

Times cited : (19)

References (37)

1
- 34247232126
- Part 97 in the series Studies on novel synthetic methodologies. IICT Communication No. 061117.
- Part 97 in the series "Studies on novel synthetic methodologies." IICT Communication No. 061117.

2
- 33947470048
- a) R. E. Parker, N. S. Isaacs, Chem. Rev. 1959, 59, 737.
- (1959) Chem. Rev , vol.59 , pp. 737
- Parker, R.E.¹ Isaacs, N.S.²

3
- 0000567366
- ed. by B. M. Trost, I. Fleming, Pergamon, Oxford
- b) J. E. G. Kemp, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, Pergamon, Oxford, 1991, Vol. 7, p. 469.
- (1991) Comprehensive Organic Synthesis , vol.7 , pp. 469
- Kemp, J.E.G.¹

4
- 33748605775
- c) D. Tanner, Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
- (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 599
- Tanner, D.¹

5
- 0002144535
- ed. by P. J. Scheuer, Academic Press, New York, Chap. 2, pp
- a) R. E. Moore, in Marine Natural Products, ed. by P. J. Scheuer, Academic Press, New York, 1978, Vol. 1, Chap. 2, pp. 43-121.
- (1978) Marine Natural Products , vol.1 , pp. 43-121
- Moore, R.E.¹

6
- 0032537156
- b) G. Righi, T. Franchini, C. Bonini, Tetrahedron Lett. 1998, 39, 2385.
- (1998) Tetrahedron Lett , vol.39 , pp. 2385
- Righi, G.¹ Franchini, T.² Bonini, C.³

7
- 0037436989
- c) S. Boukhris, A. Souizi, Tetrahedron Lett. 2003, 44, 3259.
- (2003) Tetrahedron Lett , vol.44 , pp. 3259
- Boukhris, S.¹ Souizi, A.²

8
- 0000055248
- a) C. A. Stewart, C. A. Vander Werf, J. Am. Chem. Soc. 1954, 76, 1259.
- (1954) J. Am. Chem. Soc , vol.76 , pp. 1259
- Stewart, C.A.¹ Vander Werf, C.A.²

9
- 34247213412
- b) C. Einhorn, J. L. Luche, J. Chem. Soc., Chem. Commun. 1986, 1363.
- (1986) J. Chem. Soc., Chem. Commun , pp. 1363
- Einhorn, C.¹ Luche, J.L.²

10
- 0026472697
- c) M. I. Konaklieva, M. L. Dahi, E. Turos, Tetrahedron Lett. 1992, 33, 7093.
- (1992) Tetrahedron Lett , vol.33 , pp. 7093
- Konaklieva, M.I.¹ Dahi, M.L.² Turos, E.³

11
- 0026470299
- d) I. Shibata, N. Yoshimura, A. Baba, H. Matsuda, Tetrahedron Lett. 1992, 33, 7149.
- (1992) Tetrahedron Lett , vol.33 , pp. 7149
- Shibata, I.¹ Yoshimura, N.² Baba, A.³ Matsuda, H.⁴

12
- 33644884092
- e) M. Shimizu, A. Yoshida, T. Fujisawa, Synlett 1992, 204.
- (1992) Synlett , pp. 204
- Shimizu, M.¹ Yoshida, A.² Fujisawa, T.³

13
- 0029921901
- f) H. Kotsuki, T. Shimanouchi, Tetrahedron Lett. 1996, 37, 1845.
- (1996) Tetrahedron Lett , vol.37 , pp. 1845
- Kotsuki, H.¹ Shimanouchi, T.²

14
- 0030460679
- g) N. Iranpoor, T. Tarrian, Z. Movahedi, Synthesis 1996, 1473.
- (1996) Synthesis , pp. 1473
- Iranpoor, N.¹ Tarrian, T.² Movahedi, Z.³

15
- 0029921901
- h) H. Kotsuki, T. Shimanouchi, Tetrahedron Lett. 1996, 37, 1845.
- (1996) Tetrahedron Lett , vol.37 , pp. 1845
- Kotsuki, H.¹ Shimanouchi, T.²

16
- 0035806338
- i) G. Sabitha, R. S. Babu, M. Rajkumar, C. S. Reddy, J. S. Yadav, Tetrahedron Lett. 2001, 42, 3955.
- (2001) Tetrahedron Lett , vol.42 , pp. 3955
- Sabitha, G.¹ Babu, R.S.² Rajkumar, M.³ Reddy, C.S.⁴ Yadav, J.S.⁵

17
- 0037157814
- j) M. A. Reddy, K. Surendra, N. Bhanumathi, K. R. Rao, Tetrahedron 2002, 58, 6003.
- (2002) Tetrahedron , vol.58 , pp. 6003
- Reddy, M.A.¹ Surendra, K.² Bhanumathi, N.³ Rao, K.R.⁴

18
- 0141619393
- k) H. Sharghi, M. M. Eskandari, Tetrahedron 2003, 59, 8509.
- (2003) Tetrahedron , vol.59 , pp. 8509
- Sharghi, H.¹ Eskandari, M.M.²

19
- 27144491581
- A. McCluskey, S. K. Leitch, J. Garner, C. E. Caden, T. A. Hill, L. R. Odell, S. G. Stewart, Tetrahedron Lett. 2005, 46, 8229.
- (2005) Tetrahedron Lett , vol.46 , pp. 8229
- McCluskey, A.¹ Leitch, S.K.² Garner, J.³ Caden, C.E.⁴ Hill, T.A.⁵ Odell, L.R.⁶ Stewart, S.G.⁷

20
- 1242270581
- a) L.-W. Xu, L. Li, C.-G. Xia, P.-Q. Zhao, Tetrahedron Lett. 2004, 45, 2435.
- (2004) Tetrahedron Lett , vol.45 , pp. 2435
- Xu, L.-W.¹ Li, L.² Xia, C.-G.³ Zhao, P.-Q.⁴

21
- 0141519627
- b) L.-S. Wang, T. K. Hollis, Org. Lett. 2003, 5, 2543.
- (2003) Org. Lett , vol.5 , pp. 2543
- Wang, L.-S.¹ Hollis, T.K.²

22
- 23844479521
- c) K. Surendra, N. S. Krishnaveni, Y. D. V. Nageswar, K. R. Rao, Synth. Commun. 2005, 35, 2195.
- (2005) Synth. Commun , vol.35 , pp. 2195
- Surendra, K.¹ Krishnaveni, N.S.² Nageswar, Y.D.V.³ Rao, K.R.⁴

23
- 0000048225
- d) S. E. Denmark, P. A. Barsanti, J. Org. Chem. 1998, 63, 2428.
- (1998) J. Org. Chem , vol.63 , pp. 2428
- Denmark, S.E.¹ Barsanti, P.A.²

24
- 0030894808
- e) N. Iranpoor, O. Salehi, Synth. Commun. 1997, 27, 1247.
- (1997) Synth. Commun , vol.27 , pp. 1247
- Iranpoor, N.¹ Salehi, O.²

25
- 0034841177
- a) J. S. Yadav, B. V. S. Reddy, G. M. Kumar, Synlett 2001, 1417.
- (2001) Synlett , pp. 1417
- Yadav, J.S.¹ Reddy, B.V.S.² Kumar, G.M.³

26
- 18844399915
- b) M. K. Ghorai, K. Das, A. Kumar, K. Ghosh, Tetrahedron Lett. 2005, 46, 4103.
- (2005) Tetrahedron Lett , vol.46 , pp. 4103
- Ghorai, M.K.¹ Das, K.² Kumar, A.³ Ghosh, K.⁴

27
- 66749083344
- Inorganic Chemistry
- 3rd ed, Row, Singapore
- J. E. Huheey, Inorganic Chemistry, 3rd ed., Roger and Harper Row, Singapore, 1990.
- (1990) Roger and Harper
- Huheey, J.E.¹

28
- 0000563068
- a) K. P. Chary, S. Raja Ram, D. S. Iyengar, Synlett 2000, 683.
- (2000) Synlett , pp. 683
- Chary, K.P.¹ Raja Ram, S.² Iyengar, D.S.³

29
- 0035179692
- b) J. S. Yadav, B. V. S. Reddy, K. S. Roy, K. B. Reddy, A. R. Prasad, Synthesis 2001, 2277.
- (2001) Synthesis , pp. 2277
- Yadav, J.S.¹ Reddy, B.V.S.² Roy, K.S.³ Reddy, K.B.⁴ Prasad, A.R.⁵

30
- 2342483630
- c) G. Smitha, Ch. S. Reddy, Synthesis 2004, 834.
- (2004) Synthesis , pp. 834
- Smitha, G.¹ Reddy, C.S.²

31
- 1642359808
- d) A. K. Chakraborti, R. Gulhane, Synlett 2004, 627.
- (2004) Synlett , pp. 627
- Chakraborti, A.K.¹ Gulhane, R.²

32
- 13544269532
- e) B. Das, V. S. Reddy, Chem. Lett. 2004, 33, 1428.
- (2004) Chem. Lett , vol.33 , pp. 1428
- Das, B.¹ Reddy, V.S.²

33
- 13544266446
- f) B. Das, M. R. Reddy, V. S. Reddy, R. Ramu, Chem. Lett. 2004, 33, 1526.
- (2004) Chem. Lett , vol.33 , pp. 1526
- Das, B.¹ Reddy, M.R.² Reddy, V.S.³ Ramu, R.⁴

34
- 17444394467
- a) M. Easwaramurthy, R. Ravikumar, A. J. Lakshmanan, G. J. Raju, Indian J. Chem., Sect. B 2005, 44, 635.
- (2005) Indian J. Chem., Sect. B , vol.44 , pp. 635
- Easwaramurthy, M.¹ Ravikumar, R.² Lakshmanan, A.J.³ Raju, G.J.⁴

35
- 23844558048
- b) T. Yakaiah, G. V. Reddy, B. P. V. Lingaiah, P. S. Rao, B. Narsaiah, Indian J. Chem., Sect. B 2005, 44, 1301.
- (2005) Indian J. Chem., Sect. B , vol.44 , pp. 1301
- Yakaiah, T.¹ Reddy, G.V.² Lingaiah, B.P.V.³ Rao, P.S.⁴ Narsaiah, B.⁵

36
- 9944221561
- c) R. Ghosh, S. Maiti, A. Chakraborty, Tetrahedron Lett. 2005, 46, 147.
- (2005) Tetrahedron Lett , vol.46 , pp. 147
- Ghosh, R.¹ Maiti, S.² Chakraborty, A.³

37
- 34247281565
- General experimental procedure: To a solution of an epoxide or W-tosylaziridine (1mmol) in MeCN (5 mL) ZrOCl2 (1.2 mmol) was added and the mixture was stirred at room temperature. After completion of the reaction (TLC) the mixture was diluted with EtOAc (10 mL) followed by washing with brine (20 mL) and water (2 × 10 mL, The organic portion was dried and concentrated. The crude material was purified by column chromatography (silica gel, hexane-EtOAc) to furnish pure β-chlorohydrin or N-tosyl-β-chloroamine. The spectral (IR, 1HNMR and MS) and analytical data of some representative products are given below. Product 2a: 1H NMR (CDCl3, 200 MHz, δ 7.40-7.28 (5H, m, 4.89 (1H, t, J, 7.0Hz, 3.88-3.76 (2H, m, 2.83 (1H, brs, FABMS: m/z 159, 157 [M, H]+̇, Anal. Calcd for C8H9ClO: C, 61.34; H, 5.75, Found: C, 61.46; H, 5.64, Product 2g: 1HNMR CDCl3
- 2S: C, 54.26; H, 6.26; N, 4.87%. Found: C, 54.38; H, 6.32; N, 4.81%.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.