SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3917-3921

A chemoenzymatic dynamic kinetic resolution approach to enantiomerically pure (R)- and (S)-duloxetine

(3) Träff, Annika a Lihammar, Richard a Bäckvall, Jan E a

a STOCKHOLM UNIVERSITY (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDA ANTARCTICA LIPASE B; DULOXETINE; DYNAMIC KINETIC RESOLUTION; HIGH YIELD; RUTHENIUM CATALYSTS; SYNTHETIC ROUTES; TOTAL SYNTHESIS;

ENANTIOSELECTIVITY;

RUTHENIUM;

CANDIDA ANTARCTICA LIPASE B; DULOXETINE; FUNGAL ENZYME; HYDROXYNITRILE LYASE; LIPASE B; RAC PROTEIN; RUTHENIUM; SUBTILISIN; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ANTARCTICA; CATALYST; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOMER; ENZYME KINETICS; ENZYME MECHANISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; STEREOCHEMISTRY;

KINETICS; LIPASE; RUTHENIUM; STEREOISOMERISM; THIOPHENES;

EID: 79956069868 PISSN: 00223263 EISSN: 15206904 Source Type: Journal
DOI: 10.1021/jo2003665 Document Type: Article

Times cited : (74)

References (39)

1
- 77953665611
- Norman, T. R.; Olver, J. S. Drug Des., Dev. Ther. 2010, 4, 19-31
- (2010) Drug Des., Dev. Ther. , vol.4 , pp. 19-31
- Norman, T.R.¹ Olver, J.S.²

2
- 0344927047
- Bymaster, F. P.; Beedle, E. E.; Findlay, J.; Gallagher, P. T.; Krushinski, J. H.; Mitchell, S.; Robertson, D. W.; Thompson, D. C.; Wallace, L.; Wong, D. T. Bioorg. Med. Chem. Lett. 2003, 13, 4477-4480
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 4477-4480
- Bymaster, F.P.¹ Beedle, E.E.² Findlay, J.³ Gallagher, P.T.⁴ Krushinski, J.H.⁵ Mitchell, S.⁶ Robertson, D.W.⁷ Thompson, D.C.⁸ Wallace, L.⁹ Wong, D.T.¹⁰

3
- 69949151009
- Cashman, J. R.; Ghirmai, S. Bioorg. Med. Chem. 2009, 17, 6890-6897
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 6890-6897
- Cashman, J.R.¹ Ghirmai, S.²

4
- 1842578074
- Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kesseler, M.; Stuermer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788-824
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 788-824
- Breuer, M.¹ Ditrich, K.² Habicher, T.³ Hauer, B.⁴ Kesseler, M.⁵ Stuermer, R.⁶ Zelinski, T.⁷

5
- 0025604254
- Deeter, J.; Frazier, J.; Staten, G.; Staszak, M.; Weigel, L. Tetrahedron Lett. 1990, 31, 7101-7104
- (1990) Tetrahedron Lett. , vol.31 , pp. 7101-7104
- Deeter, J.¹ Frazier, J.² Staten, G.³ Staszak, M.⁴ Weigel, L.⁵

6
- 0028928431
- Wheeler, W. J.; Kuo, F. J. Labelled Compd. Radiopharm. 1995, 36, 213-223
- (1995) J. Labelled Compd. Radiopharm. , vol.36 , pp. 213-223
- Wheeler, W.J.¹ Kuo, F.²

7
- 19344372011
- Wang, G.; Liu, X.; Zhao, G. Tetrahedron: Asymmetry 2005, 16, 1873-1879
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1873-1879
- Wang, G.¹ Liu, X.² Zhao, G.³

8
- 77958468796
- Kwak, S. H.; Seo, J. M.; Lee, K.-I. ARKIVOC 2010, 55-61
- (2010) ARKIVOC , pp. 55-61
- Kwak, S.H.¹ Seo, J.M.² Lee, K.-I.³

9
- 37549042412
- He, S. Z.; Li, X. M.; Dai, J.; Yan, M. Chin. Chem. Lett. 2008, 19, 23-25
- (2008) Chin. Chem. Lett. , vol.19 , pp. 23-25
- He, S.Z.¹ Li, X.M.² Dai, J.³ Yan, M.⁴

10
- 33750136529
- Fujima, Y.; Ikunaka, M.; Inoue, T.; Matsumoto, J. Org. Process Res. Dev. 2006, 10, 905-913
- (2006) Org. Process Res. Dev. , vol.10 , pp. 905-913
- Fujima, Y.¹ Ikunaka, M.² Inoue, T.³ Matsumoto, J.⁴

11
- 0038544136
- Sakai, K.; Sakurai, R.; Yuzawa, A.; Kobayashi, Y.; Saigo, K. Tetrahedron: Asymmetry 2003, 14, 1631-1636
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1631-1636
- Sakai, K.¹ Sakurai, R.² Yuzawa, A.³ Kobayashi, Y.⁴ Saigo, K.⁵

12
- 0033982110
- Liu, H.; Hoff, B. H.; Anthonsen, T. Chirality 2000, 12, 26-29
- (2000) Chirality , vol.12 , pp. 26-29
- Liu, H.¹ Hoff, B.H.² Anthonsen, T.³

13
- 0038443005
- Kamal, A.; Khanna, G. B. R.; Ramu, R.; Krishnaji, T. Tetrahedron Lett. 2003, 44, 4783-4787
- (2003) Tetrahedron Lett. , vol.44 , pp. 4783-4787
- Kamal, A.¹ Khanna, G.B.R.² Ramu, R.³ Krishnaji, T.⁴

14
- 43649085325
- Kamal, A.; Malik, M. S.; Shaik, A. A.; Azeeza, S. Tetrahedron: Asymmetry 2008, 19, 1078-1083
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1078-1083
- Kamal, A.¹ Malik, M.S.² Shaik, A.A.³ Azeeza, S.⁴

15
- 63249107465
- Kamal, A.; Malik, M. S.; Shaik, A. A.; Azeeza, S. J. Mol. Catal. B: Enzym. 2009, 58, 132-137
- (2009) J. Mol. Catal. B: Enzym. , vol.58 , pp. 132-137
- Kamal, A.¹ Malik, M.S.² Shaik, A.A.³ Azeeza, S.⁴

16
- 57249106473
- For reviews on DKR
- For reviews on DKR, see: Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321-331
- (2001) Chem. Soc. Rev. , vol.30 , pp. 321-331
- Huerta, F.F.¹ Minidis, A.B.E.² Bäckvall, J.-E.³

17
- 0036898158
- Kim, M.-J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2002, 13, 578-587
- (2002) Curr. Opin. Biotechnol. , vol.13 , pp. 578-587
- Kim, M.-J.¹ Ahn, Y.² Park, J.³

18
- 0041878694
- Pàmies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247-3262
- (2003) Chem. Rev. , vol.103 , pp. 3247-3262
- Pàmies, O.¹ Bäckvall, J.-E.²

19
- 34047148042
- Martín-Matute, B.; Bäckvall, J.-E. Curr. Opin. Chem. Biol. 2007, 11, 226-232
- (2007) Curr. Opin. Chem. Biol. , vol.11 , pp. 226-232
- Martín-Matute, B.¹ Bäckvall, J.-E.²

20
- 39649107133
- Ahn, Y.; Ko, S.-B.; Kim, M.-J.; Park, J. Coord. Chem. Rev. 2008, 252, 647-658
- (2008) Coord. Chem. Rev. , vol.252 , pp. 647-658
- Ahn, Y.¹ Ko, S.-B.² Kim, M.-J.³ Park, J.⁴

21
- 76449120234
- Lee, J. H.; Han, K.; Kim, M.-J.; Park, J. Eur. J. Org. Chem. 2010, 999-1015
- (2010) Eur. J. Org. Chem. , pp. 999-1015
- Lee, J.H.¹ Han, K.² Kim, M.-J.³ Park, J.⁴

22
- 21044443212
- Martín-Matúte, B.; Edin, M.; Bogar, K.; Kaynak, F. B.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 8817-8825
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8817-8825
- Martín-Matúte, B.¹ Edin, M.² Bogar, K.³ Kaynak, F.B.⁴ Bäckvall, J.-E.⁵

23
- 79952164198
- For a recent related efficient DKR of secondary alcohols
- For a recent related efficient DKR of secondary alcohols, see: Päiviö, M.; Mavrynsky, D.; Leino, R.; Kanerva, L. T. Eur. J. Org. Chem. 2011, 1452 - 1457.
- (2011) Eur. J. Org. Chem. , pp. 1452-1457
- Päiviö, M.¹ Mavrynsky, D.² Leino, R.³ Kanerva, L.T.⁴

24
- 63749090004
- Thalén, L. K.; Zhao, D.; Sortais, J.-B.; Paetzold, J.; Hoben, C.; Bäckvall, J.-E. Chem. - Eur. J. 2009, 15, 3403-3410
- (2009) Chem. - Eur. J. , vol.15 , pp. 3403-3410
- Thalén, L.K.¹ Zhao, D.² Sortais, J.-B.³ Paetzold, J.⁴ Hoben, C.⁵ Bäckvall, J.-E.⁶

25
- 1942469515
- Edin, M.; Steinreiber, J.; Bäckvall, J.-E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5761-5766
- (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5761-5766
- Edin, M.¹ Steinreiber, J.² Bäckvall, J.-E.³

26
- 47049098712
- Leijondahl, K.; Borén, L.; Braun, R.; Bäckvall, J.-E. Org. Lett. 2008, 10, 2027-2030
- (2008) Org. Lett. , vol.10 , pp. 2027-2030
- Leijondahl, K.¹ Borén, L.² Braun, R.³ Bäckvall, J.-E.⁴

27
- 65549163569
- Borén, L.; Leijondahl, K.; Bäckvall, J.-E. Tetrahedron Lett. 2009, 50, 3237-3240
- (2009) Tetrahedron Lett. , vol.50 , pp. 3237-3240
- Borén, L.¹ Leijondahl, K.² Bäckvall, J.-E.³

28
- 78049380161
- Millet, R.; Träff, A.; Petrus, M.; Bäckvall, J.-E. J. Am. Chem. Soc. 2010, 132, 15182-15184
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15182-15184
- Millet, R.¹ Träff, A.² Petrus, M.³ Bäckvall, J.-E.⁴

29
- 0346312265
- Correction: see ref 10b.; Adv. Synth. Catal. 2002, 344, 947-952
- Pàmies, O.; Bäckvall, J.-E. Adv. Synth. Catal. 2001, 343, 726-731 Correction: see ref 10b. Pàmies, O.; Bäckvall, J.-E. Adv. Synth. Catal. 2002, 344, 947-952
- (2001) Adv. Synth. Catal. , vol.343 , pp. 726-731
- Pàmies, O.¹ Bäckvall, J.-E.² Pàmies, O.³ Bäckvall, J.-E.⁴

30
- 33751499686
- Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665
- (1991) J. Org. Chem. , vol.56 , pp. 2656-2665
- Kazlauskas, R.J.¹ Weissfloch, A.N.E.² Rappaport, A.T.³ Cuccia, L.A.⁴

31
- 0343196675
- Kazlauskas, R. J.; Weissfloch, A. N. E. J. Mol. Catal. B: Enzym. 1997, 3, 65-72
- (1997) J. Mol. Catal. B: Enzym. , vol.3 , pp. 65-72
- Kazlauskas, R.J.¹ Weissfloch, A.N.E.²

32
- 70350118819
- Turcu, M. C.; Perkiö, P.; Kanerva, L. T. ARKIVOC 2009, 251-263
- (2009) ARKIVOC , pp. 251-263
- Turcu, M.C.¹ Perkiö, P.² Kanerva, L.T.³

33
- 79956100258
- See the Experimental Section for experimental details
- See the Experimental Section for experimental details.

34
- 20444448921
- Magnusson, A. O.; Rotticci-Mulder, J. C.; Santagostino, A.; Hult, K. ChemBioChem 2005, 6, 1051-1056
- (2005) ChemBioChem , vol.6 , pp. 1051-1056
- Magnusson, A.O.¹ Rotticci-Mulder, J.C.² Santagostino, A.³ Hult, K.⁴

35
- 22744445622
- Magnusson, A. O.; Takwa, M.; Hamberg, A.; Hult, K. Angew. Chem., Int. Ed. 2005, 44, 4582-4585
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4582-4585
- Magnusson, A.O.¹ Takwa, M.² Hamberg, A.³ Hult, K.⁴

36
- 78650092281
- Engström, K.; Vallin, M.; Syrén, P.-O.; Hult, K.; Bäckvall, J.-E. Org. Biomol. Chem. 2011, 9, 81-82
- (2011) Org. Biomol. Chem. , vol.9 , pp. 81-82
- Engström, K.¹ Vallin, M.² Syrén, P.-O.³ Hult, K.⁴ Bäckvall, J.-E.⁵

37
- 79956122229
- note
- D = +110.5 (c 1.1, MeOH, 95% ee (S)- 5)

38
- 29344468620
- Borén, L.; Martín-Matute, B.; Xu, Y.; Córdova, A.; Bäckvall, J.-E. Chem. - Eur. J. 2006, 12, 225-232
- (2006) Chem. - Eur. J. , vol.12 , pp. 225-232
- Borén, L.¹ Martín-Matute, B.² Xu, Y.³ Córdova, A.⁴ Bäckvall, J.-E.⁵

39
- 33750958007
- Panunzio, M.; Tamanini, E.; Bandini, E.; Campana, E.; DAurizio, A.; Vicennati, P. Tetrahedron 2006, 62, 12270-12280
- (2006) Tetrahedron , vol.62 , pp. 12270-12280
- Panunzio, M.¹ Tamanini, E.² Bandini, E.³ Campana, E.⁴ Daurizio, A.⁵ Vicennati, P.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.