SCOPUS 정보 검색 플랫폼

Volumn , Issue 14, 2008, Pages 2150-2154

Titanium(IV)(salen) and yanadium(V)(salen) complexes derived from C 2- and C1-symmetric diamines for asymmetric cyanohydrin synthesis

(3) Belokon', Yuri N b Hunt, Jamie a North, Michael a

a NEWCASTLE UNIVERSITY (United Kingdom)

b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS (Russian Federation)

Author keywords

Asymmetric catalysis; Cyanohydrins; Homogenous catalysis; Schiff bases; Titanium

Indexed keywords

ALDEHYDE; BENZALDEHYDE; CYANIDE; CYANOHYDRIN; DIAMINE DERIVATIVE; TITANIUM; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG; VANADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 51149098119 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077900 Document Type: Article

Times cited : (13)

References (35)

1
- 0037449629
- For reviews of the development and applications of these catalysts, see: a
- For reviews of the development and applications of these catalysts, see: (a) North, M. Tetrahedron: Asymmetry 2003, 14, 147.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 147
- North, M.¹

2
- 23644449360
- (b) Achard, T. R. J.; Clutterbuck, L. A.; North, M. Synlett 2005, 1828.
- (2005) Synlett , pp. 1828
- Achard, T.R.J.¹ Clutterbuck, L.A.² North, M.³

3
- 0033611986
- (a) Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 3968
- Belokon', Y.N.¹ Caveda-Cepas, S.² Green, B.³ Ikonnikov, N.S.⁴ Khrustalev, V.N.⁵ Larichev, V.S.⁶ Moscalenko, M.A.⁷ North, M.⁸ Orizu, C.⁹ Tararov, V.I.¹⁰ Tasinazzo, M.¹¹ Timofeeva, G.I.¹² Yashkina, L.V.¹³

4
- 0001636518
- (b) Belokon', Y. N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617.
- (2000) Org. Lett , vol.2 , pp. 1617
- Belokon', Y.N.¹ North, M.² Parsons, T.³

5
- 0035924929
- (c) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
- (2001) Tetrahedron , vol.57 , pp. 771
- Belokon', Y.N.¹ Green, B.² Ikonnikov, N.S.³ North, M.⁴ Parsons, T.⁵ Tararov, V.I.⁶

6
- 33750592566
- (d) Belokon', Y. N.; Maleev, V. I.; North, M.; Usanov, D. L. Chem. Commun. 2006, 4614.
- (2006) Chem. Commun , pp. 4614
- Belokon', Y.N.¹ Maleev, V.I.² North, M.³ Usanov, D.L.⁴

7
- 33750399438
- and references therein
- Belokon', Y. N.; Blacker, A. J.; Clutterbuck, L. A.; Hogg, D.; North, M.; Reeve, C. Eur. J. Org. Chem. 2006, 4609; and references therein.
- (2006) Eur. J. Org. Chem , pp. 4609
- Belokon', Y.N.¹ Blacker, A.J.² Clutterbuck, L.A.³ Hogg, D.⁴ North, M.⁵ Reeve, C.⁶

8
- 0344496716
- (a) Belokon', Y. N.; Blacker, J.; Clutterbuck, L. A.; North, M. Org. Lett. 2003, 5, 4505.
- (2003) Org. Lett , vol.5 , pp. 4505
- Belokon', Y.N.¹ Blacker, J.² Clutterbuck, L.A.³ North, M.⁴

9
- 33646915042
- (b) Belokon', Y. N.; Ishibashi, E.; Nomura, H.; North, M. Chem. Commun. 2006, 1775.
- (2006) Chem. Commun , pp. 1775
- Belokon', Y.N.¹ Ishibashi, E.² Nomura, H.³ North, M.⁴

10
- 34547798449
- (c) Belokon, Y. N.; Clegg, W.; Harrington, R. W.; Ishibashi, E.; Nomura, H.; North, M. Tetrahedron 2007, 63, 9724.
- (2007) Tetrahedron , vol.63 , pp. 9724
- Belokon, Y.N.¹ Clegg, W.² Harrington, R.W.³ Ishibashi, E.⁴ Nomura, H.⁵ North, M.⁶

11
- 0033550302
- Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 40, 8147.
- (1999) Tetrahedron Lett , vol.40 , pp. 8147
- Belokon', Y.N.¹ Green, B.² Ikonnikov, N.S.³ North, M.⁴ Tararov, V.I.⁵

12
- 0345993701
- (a) Stinson, S. C. Chem. Eng. News 2001, 79, 35.
- (2001) Chem. Eng. News , vol.79 , pp. 35
- Stinson, S.C.¹

13
- 0041590743
- (b) Gröger, H. Adv. Synth. Catal. 2001, 343, 547.
- (2001) Adv. Synth. Catal , vol.343 , pp. 547
- Gröger, H.¹

14
- 21244487101
- (c) Blacker, A. J.; North, M. Chem. Ind. (London) 2005, 22.
- (2005) Chem. Ind. (London) , pp. 22
- Blacker, A.J.¹ North, M.²

15
- 33750368763
- Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
- (1994) J. Org. Chem , vol.59 , pp. 1939
- Larrow, J.F.¹ Jacobsen, E.N.² Gao, Y.³ Hong, Y.⁴ Nie, X.⁵ Zepp, C.M.⁶

16
- 0026075037
- (a) Neumann, W. L.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865.
- (1991) Tetrahedron Lett , vol.32 , pp. 5865
- Neumann, W.L.¹ Rogic, M.M.² Dunn, T.J.³

17
- 0028302737
- (b) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
- (1994) Tetrahedron Lett , vol.35 , pp. 3391
- Bambridge, K.¹ Begley, M.J.² Simpkins, N.S.³

18
- 0001651690
- (c) Alvaro, G.; Grepioni, F.; Savoia, D. J. Org. Chem. 1997, 62, 4180.
- (1997) J. Org. Chem , vol.62 , pp. 4180
- Alvaro, G.¹ Grepioni, F.² Savoia, D.³

19
- 0032980393
- (d) Roland, S.; Mangeney, P.; Alexakis, A. Synthesis 1999, 228.
- (1999) Synthesis , pp. 228
- Roland, S.¹ Mangeney, P.² Alexakis, A.³

20
- 0000862115
- (a) Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337.
- (1996) Synlett , pp. 337
- Pan, W.¹ Feng, X.² Gong, L.³ Hu, W.⁴ Li, Z.⁵ Mi, A.⁶ Jiang, Y.⁷

21
- 0030767708
- (b) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327.
- (1997) Tetrahedron , vol.53 , pp. 14327
- Jiang, Y.¹ Gong, L.² Feng, X.³ Hu, W.⁴ Pan, W.⁵ Li, Z.⁶ Mi, A.⁷

22
- 0002350742
- Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387.
- (1998) Chem. Commun , pp. 387
- Tararov, V.I.¹ Hibbs, D.E.² Hursthouse, M.B.³ Ikonnikov, N.S.⁴ Malik, K.M.A.⁵ North, M.⁶ Orizu, C.⁷ Belokon', Y.N.⁸

23
- 51149093762
- Benzaldehyde (0.10 mL, 0.98 mmol) and catalyst 5, 6, 8, or 9 (0.1-10 mol, were dissolved in freshly distilled CH2Cl 2 (5 mL, Trimethylsilyl cyanide (0.14 mL, 1.08 mmol, 1.1 equiv) was added, and the reaction was stirred at r.t. overnight. The resulting solution was filtered through a pad of SiO2 using CH2Cl2 as eluent. Solvent was removed in vacuo to give mandelonitrile trimethylsilyl ether as a yellow oil. The conversion was determined by 1H NMR spectroscopy. The mandelonitrile trimethylsilyl ether and Sc(OTf)3 (1 mol, were then dissolved in MeCN (5 mL, and Ac2O (2.0 equiv) was added. The reaction mixture was stirred at r.t. for 20 min, then filtered through a pad of SiO2 using CH2Cl2 as eluent. Solvent was removed in vacuo to give mandelonitrile acetate as a yellow oil which was analysed by chiral GC to determine its ee
- 2 as eluent. Solvent was removed in vacuo to give mandelonitrile acetate as a yellow oil which was analysed by chiral GC to determine its ee.

24
- 0037068121
- Norsikian, S.; Holmes, I.; Lagasse, F.; Kagan, H. B. Tetrahedron Lett. 2002, 43, 5715.
- (2002) Tetrahedron Lett , vol.43 , pp. 5715
- Norsikian, S.¹ Holmes, I.² Lagasse, F.³ Kagan, H.B.⁴

25
- 34247881749
- For a discussion of the stereochemistry of octahedral metal complexes bearing salen ligands as it applies to asymmetric cyanohydrin synthesis, see: Belokon, Y. N, Clegg, W, Harrington, R. W, Young, C, North, M. Tetrahedron 2007, 63, 5287
- For a discussion of the stereochemistry of octahedral metal complexes bearing salen ligands as it applies to asymmetric cyanohydrin synthesis, see: Belokon', Y. N.; Clegg, W.; Harrington, R. W.; Young, C.; North, M. Tetrahedron 2007, 63, 5287.

26
- 1642379004
- (a) Belokon', Y. N.; Fuentes, J.; North, M.; Steed, J. W. Tetrahedron 2004, 60, 3191.
- (2004) Tetrahedron , vol.60 , pp. 3191
- Belokon', Y.N.¹ Fuentes, J.² North, M.³ Steed, J.W.⁴

27
- 4644271697
- (b) Darensbourg, D. J.; Mackiewicz, R. M.; Rodgers, J. L.; Fang, C. C.; Billodeaux, D. R.; Reibenspies, J. H. Inorg. Chem. 2004, 43, 6024.
- (2004) Inorg. Chem , vol.43 , pp. 6024
- Darensbourg, D.J.¹ Mackiewicz, R.M.² Rodgers, J.L.³ Fang, C.C.⁴ Billodeaux, D.R.⁵ Reibenspies, J.H.⁶

28
- 20944445400
- (a) Dey, S.; Karukurichi, K. R.; Shen, W.; Berkowitz, D. B. J. Am. Chem. Soc. 2005, 127, 8610.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 8610
- Dey, S.¹ Karukurichi, K.R.² Shen, W.³ Berkowitz, D.B.⁴

29
- 33744959950
- (b) Cohen, C. T.; Thomas, C. M.; Peretti, K. L.; Lobkovsky, E. B.; Coates, G. W. Dalton Trans. 2006, 237.
- (2006) Dalton Trans , pp. 237
- Cohen, C.T.¹ Thomas, C.M.² Peretti, K.L.³ Lobkovsky, E.B.⁴ Coates, G.W.⁵

30
- 33748550311
- (c) Malkov, A. V.; Gouriou, L.; Lloyd-Jones, G. C.; Star, I.; Langer, V.; Spoor, P.; Vinader, V.; Kočovsk, P. Chem. Eur. J. 2006, 12, 6910.
- (2006) Chem. Eur. J , vol.12 , pp. 6910
- Malkov, A.V.¹ Gouriou, L.² Lloyd-Jones, G.C.³ Star, I.⁴ Langer, V.⁵ Spoor, P.⁶ Vinader, V.⁷ Kočovsk, P.⁸

31
- 37049067254
- Kitaura, E.; Nishida, Y.; Okawa, H.; Kida, S. J. Chem. Soc., Dalton Trans. 1987, 3055.
- (1987) J. Chem. Soc., Dalton Trans , pp. 3055
- Kitaura, E.¹ Nishida, Y.² Okawa, H.³ Kida, S.⁴

32
- 37049087174
- (a) Cashin, B.; Cunningham, D.; Gallagher, J. F.; McArdle, P.; Higgins, T. J. Chem. Soc., Chem. Commun. 1989, 1445.
- (1989) J. Chem. Soc., Chem. Commun , pp. 1445
- Cashin, B.¹ Cunningham, D.² Gallagher, J.F.³ McArdle, P.⁴ Higgins, T.⁵

33
- 0348225268
- (b) Hoshina, G.; Tsuchimoto, M.; Ohba, S. Acta Crystallogr., Sect. C 1999, 55, 1812.
- (1999) Acta Crystallogr., Sect. C , vol.55 , pp. 1812
- Hoshina, G.¹ Tsuchimoto, M.² Ohba, S.³

34
- 33749087721
- (c) Choudhary, N. F.; Connelly, N. G.; Hitchcock, P. B.; Leigh, G. J. J. Chem. Soc, Dalton Trans. 1999, 4437.
- (1999) J. Chem. Soc, Dalton Trans , pp. 4437
- Choudhary, N.F.¹ Connelly, N.G.² Hitchcock, P.B.³ Leigh, G.J.⁴

35
- 0033788972
- (d) Tsuchimoto, M.; Hoshina, G.; Uemura, R.; Nakajima, K.; Kojima, M.; Ohba, S. Bull. Chem. Soc. Jpn. 2000, 73, 2317.
- (2000) Bull. Chem. Soc. Jpn , vol.73 , pp. 2317
- Tsuchimoto, M.¹ Hoshina, G.² Uemura, R.³ Nakajima, K.⁴ Kojima, M.⁵ Ohba, S.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.