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Volumn , Issue 1, 2009, Pages 109-111

High-yielding large-scale syntheses of enantiomerically pure NOBIN and a NOBIN-based enantiomerically pure NHC precursor

(2) Sälinger, Daniel a Brückner, Reinhard a

a UNIVERSITY OF FREIBURG (Germany)

Author keywords

BINOL; Buchwald Hartwig amination; Imidazolinium chloride; Ligand synthesis; N heterocyclic carbene; NOBIN

Indexed keywords

EID: 62349111053 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087390 Document Type: Article

Times cited : (14)

References (40)

1
- 42049108875
- Review: a
- Review: (a) Ding, K.; Li, X.; Ji, B.; Guo, H.; Kitamura, M. Curr. Org. Synth. 2005, 2, 499.
- (2005) Curr. Org. Synth , vol.2 , pp. 499
- Ding, K.¹ Li, X.² Ji, B.³ Guo, H.⁴ Kitamura, M.⁵

2
- 85064428639
- First racemic synthesis: (b) Smrčina, M.; Lorenc, M.; Hanuš, V.; Kočovský, P. Synlett 1991, 231.
- First racemic synthesis: (b) Smrčina, M.; Lorenc, M.; Hanuš, V.; Kočovský, P. Synlett 1991, 231.

3
- 0001483608
- (c) Smrčina, M.; Vyskočil, Š.; Máca, B.; Polášek, M.; Claxton, T. A.; Abbott, A. P.; Kočovský , P. J. Org. Chem. 1994, 59, 2156.
- (1994) J. Org. Chem , vol.59 , pp. 2156
- Smrčina, M.¹ Vyskočil, S.² Máca, B.³ Polášek, M.⁴ Claxton, T.A.⁵ Abbott, A.P.⁶ Kočovský, P.⁷

4
- 0010319445
- First resolution: (d) Smrčina, M.; Vyskočil, Š.; Polívková, J.; Poláková, J.; Kočovský, P. Collect. Czech. Chem. Commun. 1996, 61, 1520.
- First resolution: (d) Smrčina, M.; Vyskočil, Š.; Polívková, J.; Poláková, J.; Kočovský, P. Collect. Czech. Chem. Commun. 1996, 61, 1520.

5
- 34248585917
- Wang, C.; Jiang, Y.; Zhang, X.-X.; Huang, Y.; Li, B.-G.; Zhang, G.-L. Tetrahedron Lett. 2007, 48, 4281.
- (2007) Tetrahedron Lett , vol.48 , pp. 4281
- Wang, C.¹ Jiang, Y.² Zhang, X.-X.³ Huang, Y.⁴ Li, B.-G.⁵ Zhang, G.-L.⁶

6
- 0001757279
- Vyskočil, Š.; Jaracz, S.; Smrčina, M.; Štícha, M.; Hanuš, V.; Polášek, M.; Kočovský, P. J. Org. Chem. 1998, 63, 7727.
- (1998) J. Org. Chem , vol.63 , pp. 7727
- Vyskočil, S.¹ Jaracz, S.² Smrčina, M.³ Štícha, M.⁴ Hanuš, V.⁵ Polášek, M.⁶ Kočovský, P.⁷

7
- 0000376088
- (a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 8837
- Carreira, E.M.¹ Singer, R.A.² Lee, W.³

8
- 0000778829
- (b) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 3649
- Carreira, E.M.¹ Lee, W.² Singer, R.A.³

9
- 0001151356
- (c) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 12360
- Singer, R.A.¹ Carreira, E.M.²

10
- 0037677400
- (d) Singer, R. A.; Brock, J. R.; Carreira, E. M. Helv. Chim. Acta 2003, 86, 1040.
- (2003) Helv. Chim. Acta , vol.86 , pp. 1040
- Singer, R.A.¹ Brock, J.R.² Carreira, E.M.³

11
- 0346732030
- Ji, B.; Yuan, Y.; Ding, K.; Meng, J. Chem. Eur. J. 2003, 9, 5989.
- (2003) Chem. Eur. J , vol.9 , pp. 5989
- Ji, B.¹ Yuan, Y.² Ding, K.³ Meng, J.⁴

12
- 0038102341
- Hu, Y.; Liang, X.; Wang, J.; Zheng, Z.; Hu, X. J. Org. Chem. 2003, 68, 4542.
- (2003) J. Org. Chem , vol.68 , pp. 4542
- Hu, Y.¹ Liang, X.² Wang, J.³ Zheng, Z.⁴ Hu, X.⁵

13
- 0037090229
- Tang, W.; Hu, X.; Zhang, X. Tetrahedron Lett. 2002, 43, 3075.
- (2002) Tetrahedron Lett , vol.43 , pp. 3075
- Tang, W.¹ Hu, X.² Zhang, X.³

14
- 0037070075
- Brunner, H.; Henning, F.; Weber, M. Tetrahedron: Asymmetry 2002, 13, 37.
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 37
- Brunner, H.¹ Henning, F.² Weber, M.³

15
- 33746734915
- Mikami, K.; Kataoka, S.; Wakabayashi, K.; Aikawa, K. Tetrahedron Lett. 2006, 47, 6361.
- (2006) Tetrahedron Lett , vol.47 , pp. 6361
- Mikami, K.¹ Kataoka, S.² Wakabayashi, K.³ Aikawa, K.⁴

16
- 0037042233
- Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 4954
- Van Veldhuizen, J.J.¹ Garber, S.B.² Kingsbury, J.S.³ Hoveyda, A.H.⁴

17
- 34247201978
- Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2007, 46, 1097;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1097
- Brown, M.K.¹ May, T.L.² Baxter, C.A.³ Hoveyda, A.H.⁴

18
- 34250693599
- Angew. Chem. 2007, 119, 1115.
- (2007) Angew. Chem , vol.119 , pp. 1115

19
- 4544235332
- (a) Larsen, A. O.; Leu, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 11130
- Larsen, A.O.¹ Leu, W.² Oberhuber, C.N.³ Campbell, J.E.⁴ Hoveyda, A.H.⁵

20
- 34250704681
- (b) Kacprzynski, M. A.; May, T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2007, 46, 4554;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4554
- Kacprzynski, M.A.¹ May, T.L.² Kazane, S.A.³ Hoveyda, A.H.⁴

21
- 62349140823
- Angew. Chem. 2007, 119, 4638.
- (2007) Angew. Chem , vol.119 , pp. 4638

22
- 0141885397
- (a) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 12502
- Van Veldhuizen, J.J.¹ Gillingham, D.G.² Garber, S.B.³ Kataoka, O.⁴ Hoveyda, A.H.⁵

23
- 4644256135
- (b) Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 12288
- Gillingham, D.G.¹ Kataoka, O.² Garber, S.B.³ Hoveyda, A.H.⁴

24
- 34250718022
- (c) Cortez, G. A.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2007, 46, 4534;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4534
- Cortez, G.A.¹ Schrock, R.R.² Hoveyda, A.H.³

25
- 53549093543
- Angew. Chem. 2007, 119, 4618.
- (2007) Angew. Chem , vol.119 , pp. 4618

26
- 34547174193
- (d) Cortez, G. A.; Baxter, C. A.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2007, 9, 2871.
- (2007) Org. Lett , vol.9 , pp. 2871
- Cortez, G.A.¹ Baxter, C.A.² Schrock, R.R.³ Hoveyda, A.H.⁴

27
- 33751391553
- (a) Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917.
- (1992) J. Org. Chem , vol.57 , pp. 1917
- Smrčina, M.¹ Lorenc, M.² Hanuš, V.³ Sedmera, P.⁴ Kočovský, P.⁵

28
- 33751385309
- (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534.
- (1993) J. Org. Chem , vol.58 , pp. 4534
- Smrčina, M.¹ Poláková, J.² Vyskočil, S.³ Kočovský, P.⁴

29
- 0000441860
- Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869.
- (2001) Org. Lett , vol.3 , pp. 869
- Hon, S.-W.¹ Li, C.-H.² Kuo, J.-H.³ Barhate, N.B.⁴ Liu, Y.-H.⁵ Wang, Y.⁶ Chen, C.-T.⁷

30
- 0033524686
- Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 1095.
- (1999) Tetrahedron Lett , vol.40 , pp. 1095
- Singer, R.A.¹ Buchwald, S.L.²

31
- 62349134937
- 5 g ca. 50 € [(R)-BINOL, ABCR; (S)-BINOL, AlfaAesar), 1 kg ca
- Enantiopure BINOL
- Enantiopure BINOL: 5 g ca. 50 € [(R)-BINOL, ABCR; (S)-BINOL, AlfaAesar), 1 kg ca. 900 $ [(R)- or (S)-BINOL, AK Scientific).
- 900 $ [(R)- or (S)-BINOL, AK Scientific)

32
- 33847609216
- Ooi, T.; Ohmatsu, K.; Maruoka, K. J. Am. Chem. Soc. 2007, 129, 2410.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 2410
- Ooi, T.¹ Ohmatsu, K.² Maruoka, K.³

33
- 62349130543
- S)-BINOL monotriflate (5.59 g, 13.4 mmol) was dissolved in CH2Cl2 (35 mL) and CH2(OMe)2 (35 mL, Then P4O10 (3.93 g, 13.8 mmol, 1.03 equiv) was added within 1 h in 2 portions. The mixture was stirred at r.t. for 7 h, poured into aq NH3 (35, 30 mL, and extracted with CH2Cl2 (3 x 10 mL, The combined organic phases were dried over MgSO4. Evaporation of the solvent under reduced pressure and flash chromatography on SiO2 (eluent: cyclohexane-EtOAc, 95:5) provided the MOM-protected (S)-BINOL monotriflate 518 5.90 g, 95, as a colorless oil. It crystallized slowly when transferred into a refrigerator
- 18 (5.90 g, 95%) as a colorless oil. It crystallized slowly when transferred into a refrigerator.

34
- 0037427994
- Acetalization method: Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130.
- Acetalization method: Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130.

35
- 62349120069
- See
- See: http://www.epa.gov/ttn/atw/hlthef/chlo-eth.html.

36
- 62349099087
- A suspension of benzylamine 6 (15.9 g, 38.0 mmol) and Pd (10% on C, 2.04 g, 1.99 mmol, 5 mol, in EtOAc (70 mL) was heated under H2 (1 atm) at 60°C for 3 h. After filtration through Celite, the solvent was removed under reduced pressure. The residue was dissolved in CH 2Cl2 (100 mL) and MeOH (100 mL, Concentrated H 2SO4 (6.0 mL) was added and the mixture refluxed for 2 h. Saturated aq NaHCO3 (100 mL) was added after cooling. The mixture was extracted with CH2Cl2 (3 x 50 mL, The combined organic phases were dried over MgSO4. Evaporation of the solvent under reduced pressure provided (S)-NOBIN (1; 9.19 g, 85, as a faintly yellow solid (pure as judged by 1H NMR, Recrystallization from toluene rendered rounded white needles (8.84 g, 82, On a smaller scale (3.29 g of benzylamine 6) the yield of recrystallized 1 was 1.97 g [88, cf. footno
- 1H NMR). Recrystallization from toluene rendered rounded white needles (8.84 g, 82%). On a smaller scale (3.29 g of benzylamine 6) the yield of recrystallized 1 was 1.97 g [88%; cf. footnote (e) of Scheme 1].

37
- 62349140529
- Enantiopure NOBIN: 1 g ca. 500 € [(R)- or (S)-NOBIN, ABCR], 10 g ca. 1500 $ [(R)-NOBIN], 50 g ca. 4000 $ [(S)-NOBIN, both Shanghai FWD Chemicals].
- Enantiopure NOBIN: 1 g ca. 500 € [(R)- or (S)-NOBIN, ABCR], 10 g ca. 1500 $ [(R)-NOBIN], 50 g ca. 4000 $ [(S)-NOBIN, both Shanghai FWD Chemicals].

38
- 2342570828
- Perillo, I.; Caterina, M. C.; López, J.; Salerno, A. Synthesis 2004, 851.
- (2004) Synthesis , pp. 851
- Perillo, I.¹ Caterina, M.C.² López, J.³ Salerno, A.⁴

39
- 62349119367
- 3N) provided 10 (6.39 g, 89%) as a deep red oil.
- 3N) provided 10 (6.39 g, 89%) as a deep red oil.

40
- 62349106332
- The following conditions were adapted from a related transformation: 18 Cs2CO3 (7.51 g, 23.0 mmol, 1.30 equiv) was dried in vacuo with a heat gun for 30 min. After cooling, Pd(OAc)2 (395 mg, 1.76 mmol, 9.90 mol, o-Ph2PC6H 4)2O (1.89 g, 3.51 mmol, 20 mol, and a solution of the MOM-protected monotriflate 5 (8.22 g, 17.8 mmol) and the diamine 10 (4.09 g, 22.9 mmol, 1.29 equiv) in toluene (9 mL) were added. The suspension was degassed and stirred at 115°C for 14 h. Filtration through Celite, evaporation of the solvent under reduced pressure, and flash chromatography on SiO2 (eluent: cyclohexane-EtOAc, 90:10 → 80:20) provided the diamine 12 (7.79 g, 89, as a reddish-brown sticky solid. 1H NMR (400 MHz, CDCl3, TMS, δ, 1.91 (s, 2 x o-CH3, 2.17 (s, p-CH3, 2.95 ddd, 3J
- 3).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.