SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 5, 2008, Pages 720-724

Brønsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1,10-phenanthrolines

(3) Metallinos, Costa a Barrett, Fred B a Xu, Shufen a

a BROCK UNIVERSITY (Canada)

Author keywords

Bransted acid; Enantioselective; Organocatalysis; Phenanthroline; Reduction

Indexed keywords

2 (N ACETYL)METHYL 1,10 PHENANTHROLINE; 2 ISOPROPYL 1,10 PHENANTHROLINE; 2 METHYL 1,10 PHENANTHROLINE; 2 N BUTYL 1,10 PHENANTHROLINE; 2 PHENYL 1,10 PHENANTHROLINE; 2,2' DIHYDROXY 1,1' BINAPHTHYL; 2,9 DI N BUTYL 1,10 PHENANTHROLINE; 2,9 DIPHENYL 1,10 PHENANTHROLINE; BRONSTED ACID; DIHYDROPYRIDINE; PHENANTHROLINE DERIVATIVE; PHOSPHORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REDUCTION; STEREOCHEMISTRY;

EID: 41349095492 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032103 Document Type: Article

Times cited : (50)

References (31)

1
- 2342570203
- Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 1566
- Akiyama, T.¹ Itoh, J.² Yokota, K.³ Fuchibe, K.⁴

2
- 2342521907
- Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 5356
- Uraguchi, D.¹ Terada, M.²

3
- 31944452587
- (a) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 1086
- Seayad, J.¹ Seayad, A.M.² List, B.³

4
- 41349115235
- (b) Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2006, 128, 6756.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 6756
- Yamanaka, M.¹ Itoh, J.² Fuchibe, K.³ Akiyama, T.⁴

5
- 4644355914
- (c) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
- (2004) J. Am. Chem. Soc , vol.126 , Issue.1 , pp. 1804
- Uraguchi, D.¹ Sorimachi, K.² Terada, M.³

6
- 30744477746
- (d) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 84
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

7
- 35048880194
- (e) Wanner, M. J.; van der Haas, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem. Int. Ed. 2007, 46, 7485.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 7485
- Wanner, M.J.¹ van der Haas, R.N.S.² de Cuba, K.R.³ van Maarseveen, J.H.⁴ Hiemstra, H.⁵

8
- 33746272976
- Reviews: a
- Reviews: (a) Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3909
- Connon, S.J.¹

9
- 33745683617
- (b) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
- (2006) Adv. Synth. Catal , vol.348 , pp. 999
- Akiyama, T.¹ Itoh, J.² Fuchibe, K.³

10
- 33646468489
- (c) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1520
- Taylor, M.S.¹ Jacobsen, E.N.²

11
- 33746269442
- Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 3683.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3683
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

12
- 34250765230
- For other applications of this methodology, see: a
- For other applications of this methodology, see: (a) Rueping, M.; Antonchick, A. P. Angew. Chem. Int. Ed. 2007, 46, 4562.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4562
- Rueping, M.¹ Antonchick, A.P.²

13
- 33750148995
- (b) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 6751.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6751
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

14
- 34250760386
- (c) Rueping, M.; Sugiono, E.; Schoepke, F. R. Synlett 2007, 1441.
- (2007) Synlett , pp. 1441
- Rueping, M.¹ Sugiono, E.² Schoepke, F.R.³

15
- 34250725648
- (d) Rueping, M.; Antonchick, A. P. Angew. Chem. Int. Ed. 2007, 46, 2097.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 2097
- Rueping, M.¹ Antonchick, A.P.²

16
- 41349120196
- Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem. Int. Ed. 2006, 45, 2263.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 2263
- Lu, S.-M.¹ Wang, Y.-Q.² Han, X.-W.³ Zhou, Y.-G.⁴

17
- 4344711567
- (a) Glorius, F.; Spielkamp, N.; Holle, S.; Goddard, R.; Lehmann, C. W. Angew. Chem. Int. Ed. 2004, 43, 2850.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2850
- Glorius, F.¹ Spielkamp, N.² Holle, S.³ Goddard, R.⁴ Lehmann, C.W.⁵

18
- 21244463410
- (b) Legault, C. Y.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 8966.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 8966
- Legault, C.Y.¹ Charette, A.B.²

19
- 6444231122
- Metallinos, C.; Barrett, F. B.; Chaytor, J. L.; Heska, M. E. A. Org. Lett. 2004, 6, 3641.
- (2004) Org. Lett , vol.6 , pp. 3641
- Metallinos, C.¹ Barrett, F.B.² Chaytor, J.L.³ Heska, M.E.A.⁴

20
- 33750021145
- Metallinos, C.; Barrett, F. B.; Wang, Y.; Xu, S.; Taylor, N. J. Tetrahedron 2006, 62, 11145.
- (2006) Tetrahedron , vol.62 , pp. 11145
- Metallinos, C.¹ Barrett, F.B.² Wang, Y.³ Xu, S.⁴ Taylor, N.J.⁵

21
- 33845558509
- For preparation of 2,2′-dimethoxy-1,1′-binaphthyl, see: a
- For preparation of 2,2′-dimethoxy-1,1′-binaphthyl, see: (a) Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393.
- (1981) J. Org. Chem , vol.46 , pp. 393
- Lingenfelter, D.S.¹ Helgeson, R.C.² Cram, D.J.³

22
- 0001541416
- For preparation of 3,3′-diaryl BINOL, see: (b) Simonsen, K. B.; Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 7536.
- For preparation of 3,3′-diaryl BINOL, see: (b) Simonsen, K. B.; Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 7536.

23
- 0034613228
- (c) Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319.
- (2000) J. Org. Chem , vol.65 , pp. 6319
- Wipf, P.¹ Jung, J.-K.²

24
- 0002128702
- For preparation of 3,3′-diaryl-1,1′-binaphthyl-2,2′- diyl hydrogen phosphates, see: d
- For preparation of 3,3′-diaryl-1,1′-binaphthyl-2,2′- diyl hydrogen phosphates, see: (d) Jacques, J.; Fouquey, C. Org. Synth. 1989, 67, 1.
- (1989) Org. Synth , vol.67 , pp. 1
- Jacques, J.¹ Fouquey, C.²

25
- 0000817031
- (a) Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J.-P. Tetrahedron Lett. 1982, 23, 5291.
- (1982) Tetrahedron Lett , vol.23 , pp. 5291
- Dietrich-Buchecker, C.O.¹ Marnot, P.A.² Sauvage, J.-P.³

26
- 0037620598
- (b) Dietrich-Buchecker, C.; Colasson, B.; Fujita, M.; Hori, A.; Geum, N.; Sakamoto, S.; Yamaguchi, K.; Sauvage, J.-P. J. Am. Chem. Soc. 2003, 125, 5717.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5717
- Dietrich-Buchecker, C.¹ Colasson, B.² Fujita, M.³ Hori, A.⁴ Geum, N.⁵ Sakamoto, S.⁶ Yamaguchi, K.⁷ Sauvage, J.-P.⁸

27
- 41349092470
- Reduction of 6a with Catalyst 4b and Enantiomeric Assay A flame-dried screw-cap vial with a stir bar was charged with 6a (50 mg, 0.26 mmol, dihydropyridine 3 (390 mg, 1.54 mmol, 6 equiv, catalyst 4b (3.6 mg, 0.005 mmol, 2 mol, and dry benzene (5 mL, The vial was flushed with argon, capped, and the mixture was heated with stirring at 60°C for 24 h. The reaction mixture was transferred to a round-bottomed flask and the solvent was removed under reduced pressure. Absolute EtOH (5 mL) and KOH (2 pellets, ca. 200 mg) were added, and the mixture was heated to reflux for 45 min. Then, H2O (5 mL) was added and EtOH was removed under reduced pressure. The remaining aqueous mixture was extracted with CH2Cl 2 (3 x 5 mL) and the combined organic extract was dried over anhyd Na2SO4, filtered, and concentrated in vacuo. Column chromatography silica gel, 83:15:2 hexanes-EtOAc-Et3N; R f
- 3): δ = 152.7, 125.2, 124.7, 118.3 (2 C), 116.8, 116.7, 45.3, 38.9, 29.3, 23.4, 22.8, 20.2, 19.2.

28
- 33846932791
- Metallinos, C.; Dudding, T.; Zaifman, J.; Chaytor, J. L.; Taylor, N. J. J. Org. Chem. 2007, 72, 957.
- (2007) J. Org. Chem , vol.72 , pp. 957
- Metallinos, C.¹ Dudding, T.² Zaifman, J.³ Chaytor, J.L.⁴ Taylor, N.J.⁵

29
- 0022994766
- 2-Aminomethyl-1,10-phenanthroline was prepared according to a literature procedure: Engbersen, J. F. J.; Koudijs, A.; Joosten, M. H. A.; van der Plas, H. C. J. Heterocycl. Chem. 1986, 23, 989.
- 2-Aminomethyl-1,10-phenanthroline was prepared according to a literature procedure: Engbersen, J. F. J.; Koudijs, A.; Joosten, M. H. A.; van der Plas, H. C. J. Heterocycl. Chem. 1986, 23, 989.

30
- 41349110604
- Reduction of 6g with Catalyst 4b and Enantiomeric Assay A flame-dried screw-cap vial with a stir bar was charged with 6g (58 mg, 0.20 mmol, dihydropyridine 3 (304 mg, 1.20 mmol, 6 equiv, catalyst 4b (7 mg, 0.01 mmol, 5 mol, and dry benzene (4 mL, The vial was flushed with argon, capped, and the mixture was heated with stirring at 60°C for 24 h. The reaction mixture was transferred to a round-bottomed flask and the solvent was removed under reduced pressure. Column chromatography [silica gel, hexanes-EtOAc (97:3, gave, sequentially, 2,9-dibutyl-1,2,3,4-tetrahydro-1,10- phenanthroline (9g, 5 mg, 8, Rf, 0.39) and octahydrophenanthroline 7g (53 mg, 88, Rf, 0.19) as a 3:2 mixture of ent and meso isomers. Compound 9g: pale yellow oil. 1H NMR (300 MHz, acetone-d6, δ, 7.98 (d, 1 H, J, 8.4 Hz, 7.26 (d, 1 H, J, 8.4 Hz, 7.06 d, 1 H
- 2O: 326.2358; found: 326.2356.

31
- 30544448390
- Terada, M.; Sorimachi, K.; Uraguchi, D. Synlett 2006, 133.
- (2006) Synlett , pp. 133
- Terada, M.¹ Sorimachi, K.² Uraguchi, D.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.