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Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 6372-6376

Bisoxazolidine-catalyzed enantioselective reformatsky reaction

(2) Wolf, Christian a Moskowitz, Max a

a GEORGETOWN UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; AROMATIC SUBSTRATES; DIMETHYLZINC; ENANTIOSELECTIVE; HIGH YIELD; REFORMATSKY REACTION; ROOM TEMPERATURE;

ALDEHYDES; ORGANIC COMPOUNDS;

CATALYSIS;

ALDEHYDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BISOXAZOLIDINE; DIMETHYLZINC; ETHYL 3 (4 BROMOPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 CHLOROPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 FLUOROPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 TERT BUTYLPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 CYCLOHEXYL 3 HYDROXYPROPANOATE; ETHYL 3 HYDROXY 3 (1 NAPHTHYL)PROPANOATE; ETHYL 3 HYDROXY 3 (2 NAPHTHYL)PROPANOATE; ETHYL 3 HYDROXY 3 (4 ARYL)PROPANOATE DERIVATIVE; ETHYL 3 HYDROXY 3 (4 ISOPROPYLPHENYL)PROPANOATE; ETHYL 3 HYDROXY 3 (4 METHOXYPHENYL)PROPANOATE; ETHYL 3 HYDROXY 3 (4 TOLYL)PROPANOATE; ETHYL 3 HYDROXY 3 (THIOPHEN 2 YL)PROPANOATE; ETHYL 3 HYDROXY 3 PHENYLPROPANOATE; ETHYL 3 HYDROXY 4 METHYLPENTANOATE; ETHYL 3 HYDROXY 5 PHENYLPENTANOATE; ETHYL IODOACETATE; LIGAND; UNCLASSIFIED DRUG;

AIR; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REFORMATSKY REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 79961068882 PISSN: 00223263 EISSN: 15206904 Source Type: Journal
DOI: 10.1021/jo200774e Document Type: Article

Times cited : (28)

References (42)

1
- 0007180191
- Reformatsky, S. Ber. Dtsch. Chem. Ges. 1887, 20, 1210-1211
- (1887) Ber. Dtsch. Chem. Ges. , vol.20 , pp. 1210-1211
- Reformatsky, S.¹

2
- 34250212739
- Cozzi, P. G. Angew. Chem., Int. Ed. 2007, 46, 2568-2571
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2568-2571
- Cozzi, P.G.¹

3
- 78650150622
- Greszler, S. N.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132, 17393-17395
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 17393-17395
- Greszler, S.N.¹ Malinowski, J.T.² Johnson, J.S.³

4
- 0000825178
- Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549-2551
- (2000) Org. Lett. , vol.2 , pp. 2549-2551
- Kanai, K.¹ Wakabayashi, H.² Honda, T.³

5
- 0037189263
- Petrini, M.; Profeta, R.; Righi, P. J. Org. Chem. 2002, 67, 4530-4535
- (2002) J. Org. Chem. , vol.67 , pp. 4530-4535
- Petrini, M.¹ Profeta, R.² Righi, P.³

6
- 0037459711
- Adrian, J. C., Jr.; Snapper, M. L. J. Org. Chem. 2003, 68, 2143-2150
- (2003) J. Org. Chem. , vol.68 , pp. 2143-2150
- Adrian Jr., J.C.¹ Snapper, M.L.²

7
- 0042693261
- Hama, T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176-11177
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11176-11177
- Hama, T.¹ Liu, X.² Culkin, D.A.³ Hartwig, J.F.⁴

8
- 33646138279
- Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976-4985
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4976-4985
- Hama, T.¹ Culkin, D.A.² Hartwig, J.F.³

9
- 33744974796
- Hlavinka, M. L.; Hagadorn, J. R. Tetrahedron Lett. 2006, 47, 5049-5053
- (2006) Tetrahedron Lett. , vol.47 , pp. 5049-5053
- Hlavinka, M.L.¹ Hagadorn, J.R.²

10
- 44649187386
- Cozzi, P. G.; Mignogna, A.; Zoli, L. Pure Appl. Chem. 2008, 80, 891-901
- (2008) Pure Appl. Chem. , vol.80 , pp. 891-901
- Cozzi, P.G.¹ Mignogna, A.² Zoli, L.³

11
- 0842328443
- Clark, J. D.; Weisenburger, G. A.; Anderson, D. K.; Colson, P.-J.; Edney, A. D.; Gallagher, D. J.; Kleine, H. P.; Knable, C. M.; Lantz, M. K.; Moore, C. M. V.; Murphy, J. B.; Rogers, T. E.; Ruminski, P. G.; Shah, A. S.; Storer, N.; Wise, B. E. Org. Proc. Res. Dev 2004, 8, 51-61
- (2004) Org. Proc. Res. Dev , vol.8 , pp. 51-61
- Clark, J.D.¹ Weisenburger, G.A.² Anderson, D.K.³ Colson, P.-J.⁴ Edney, A.D.⁵ Gallagher, D.J.⁶ Kleine, H.P.⁷ Knable, C.M.⁸ Lantz, M.K.⁹ Moore, C.M.V.¹⁰ Murphy, J.B.¹¹ Rogers, T.E.¹² Ruminski, P.G.¹³ Shah, A.S.¹⁴ Storer, N.¹⁵ Wise, B.E.¹⁶

12
- 20444380392
- Orsini, F.; Sello, G.; Manzo, A. M.; Lucci, E. M. Tetrahedron: Asymm. 2005, 16, 1913-1918
- (2005) Tetrahedron: Asymm. , vol.16 , pp. 1913-1918
- Orsini, F.¹ Sello, G.² Manzo, A.M.³ Lucci, E.M.⁴

13
- 34248647878
- Yu, L.-T.; Ho, M.-T.; Chang, C.-Y.; Yang, T.-K. Tetrahedron: Asymm. 2007, 18, 949-962
- (2007) Tetrahedron: Asymm. , vol.18 , pp. 949-962
- Yu, L.-T.¹ Ho, M.-T.² Chang, C.-Y.³ Yang, T.-K.⁴

14
- 0038305107
- Fujiwara, Y.; Katagiri, T.; Uneyama, K. Tetrahedron Lett. 2003, 44, 6161-6163
- (2003) Tetrahedron Lett. , vol.44 , pp. 6161-6163
- Fujiwara, Y.¹ Katagiri, T.² Uneyama, K.³

15
- 12344249542
- Emmerson, D. P. G.; Hems, W. P.; Davis, B. G. Tetrahedron: Asymm. 2005, 16, 213-221
- (2005) Tetrahedron: Asymm. , vol.16 , pp. 213-221
- Emmerson, D.P.G.¹ Hems, W.P.² Davis, B.G.³

16
- 33746133536
- Ribeiro, C. M. R.; de Farias, F. M. C. Mini-Rev. Org. Chem. 2006, 3, 1-10
- (2006) Mini-Rev. Org. Chem. , vol.3 , pp. 1-10
- Ribeiro, C.M.R.¹ De Farias, F.M.C.²

17
- 33646465142
- Kloetzing, R. J.; Thaler, T.; Knochel, P. Org. Lett. 2006, 8, 1125-1128
- (2006) Org. Lett. , vol.8 , pp. 1125-1128
- Kloetzing, R.J.¹ Thaler, T.² Knochel, P.³

18
- 32844462096
- Shin, E.-K.; Kim, H. J.; Kim, Y.; Kim, Y.; Park, Y. S. Tetrahedron Lett. 2006, 47, 1933-1935
- (2006) Tetrahedron Lett. , vol.47 , pp. 1933-1935
- Shin, E.-K.¹ Kim, H.J.² Kim, Y.³ Kim, Y.⁴ Park, Y.S.⁵

19
- 45449109768
- Xu, X.-H.; Qiu, X.-L.; Qing, F.-L. Tetrahedron 2008, 64, 7353-7361
- (2008) Tetrahedron , vol.64 , pp. 7353-7361
- Xu, X.-H.¹ Qiu, X.-L.² Qing, F.-L.³

20
- 44449098116
- Fernandez-Ibanez, M. A.; Macia, B.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2008, 47, 1317-1319
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1317-1319
- Fernandez-Ibanez, M.A.¹ MacIa, B.² Minnaard, A.J.³ Feringa, B.L.⁴

21
- 47249141161
- Cozzi, P. G.; Benfatti, F.; Capdevila, M. G.; Mignogna, A. Chem. Commun. 2008, 3317-3318
- (2008) Chem. Commun. , pp. 3317-3318
- Cozzi, P.G.¹ Benfatti, F.² Capdevila, M.G.³ Mignogna, A.⁴

22
- 47249141882
- Cozzi, P. G.; Mignogna, A.; Vicennati, P. Adv. Synth. Catal. 2008, 350, 975-978
- (2008) Adv. Synth. Catal. , vol.350 , pp. 975-978
- Cozzi, P.G.¹ Mignogna, A.² Vicennati, P.³

23
- 33746211355
- For examples of catalytic asymmetric Reformatsky reaction with ketones, see
- For examples of catalytic asymmetric Reformatsky reaction with ketones, see: Cozzi, P. G. Angew. Chem., Int. Ed. 2006, 45, 2951-2954
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2951-2954
- Cozzi, P.G.¹

24
- 44449127193
- Fernandez-Ibanez, M. A.; Macia, B.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2008, 2571-2573
- (2008) Chem. Commun. , pp. 2571-2573
- Fernandez-Ibanez, M.A.¹ MacIa, B.² Minnaard, A.J.³ Feringa, B.L.⁴

25
- 34548690118
- Cozzi, P. G.; Mignogna, A.; Zoli, L. Synthesis 2007, 2746-2750
- (2007) Synthesis , pp. 2746-2750
- Cozzi, P.G.¹ Mignogna, A.² Zoli, L.³

26
- 55949122493
- For examples of catalytic enantioselective imino Reformatsky reaction, see:; Angew. Chem., Int. Ed. 2005, 44, 3600-3603
- Fernandez-Ibanez, M. A.; Macia, B.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2008, 10, 4041-4044 For examples of catalytic enantioselective imino Reformatsky reaction, see: Cozzi, P. G.; Rivalta, E. Angew. Chem., Int. Ed. 2005, 44, 3600-3603
- (2008) Org. Lett. , vol.10 , pp. 4041-4044
- Fernandez-Ibanez, M.A.¹ MacIa, B.² Minnaard, A.J.³ Feringa, B.L.⁴ Cozzi, P.G.⁵ Rivalta, E.⁶

27
- 33644502502
- Cozzi, P. G.; Rivalta, E. Pure Appl. Chem. 2006, 78, 287-291
- (2006) Pure Appl. Chem. , vol.78 , pp. 287-291
- Cozzi, P.G.¹ Rivalta, E.²

28
- 33750519894
- Cozzi, P. G. Adv. Synth. Catal. 2006, 348, 2075-2079
- (2006) Adv. Synth. Catal. , vol.348 , pp. 2075-2079
- Cozzi, P.G.¹

29
- 79961097174
- This ligand is commercially available at Strem (catalogue no. 07-0488), US Patent, 11/737,371.
- This ligand is commercially available at Strem (catalogue no. 07-0488), US Patent, 11/737,371, 2007.
- (2007)

30
- 79952387553
- For a general overview on bisoxazolidine catalysis, see
- For a general overview on bisoxazolidine catalysis, see: Wolf, C.; Xu, H. Chem. Commun. 2011, 47, 3339-3350
- (2011) Chem. Commun. , vol.47 , pp. 3339-3350
- Wolf, C.¹ Xu, H.²

31
- 33748058878
- Wolf, C.; Liu, S. J. Am. Chem. Soc. 2006, 128, 10996-10997
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 10996-10997
- Wolf, C.¹ Liu, S.²

32
- 34547938550
- Liu, S.; Wolf, C. Org. Lett. 2007, 9, 2965-2968
- (2007) Org. Lett. , vol.9 , pp. 2965-2968
- Liu, S.¹ Wolf, C.²

33
- 46849091451
- Liu, S.; Wolf, C. Org. Lett. 2008, 10, 1831-1834
- (2008) Org. Lett. , vol.10 , pp. 1831-1834
- Liu, S.¹ Wolf, C.²

34
- 70349907587
- Yearick Spangler, K.; Wolf, C. Org. Lett. 2009, 11, 4724-4727
- (2009) Org. Lett. , vol.11 , pp. 4724-4727
- Yearick Spangler, K.¹ Wolf, C.²

35
- 77958507858
- Xu, H.; Wolf, C. Chem. Commun. 2010, 46, 8026-8028
- (2010) Chem. Commun. , vol.46 , pp. 8026-8028
- Xu, H.¹ Wolf, C.²

36
- 78149251252
- Xu, H.; Wolf, C. Synlett 2010, 2765-2770
- (2010) Synlett , pp. 2765-2770
- Xu, H.¹ Wolf, C.²

37
- 79953041595
- Wolf, C.; Zhang, P. Adv. Synth. Catal. 2011, 353, 760-766
- (2011) Adv. Synth. Catal. , vol.353 , pp. 760-766
- Wolf, C.¹ Zhang, P.²

38
- 77956650810
- Benfatti, F.; Cozzi, P. G. Tetrahedron: Asymmetry 2010, 21, 1503-1506
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 1503-1506
- Benfatti, F.¹ Cozzi, P.G.²

39
- 0037042288
- Zhou, Y.; Tang, W.; Wang, W.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 4952-4953
- Zhou, Y.¹ Tang, W.² Wang, W.³ Li, W.⁴ Zhang, X.⁵

40
- 37049098061
- Soai, K.; Yamanoi, T.; Hikima, H.; Oyamada, H. J. Chem. Soc., Chem., Commun. 1985, 138-139
- (1985) J. Chem. Soc., Chem., Commun. , pp. 138-139
- Soai, K.¹ Yamanoi, T.² Hikima, H.³ Oyamada, H.⁴

41
- 0034708574
- Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702-1706
- (2000) J. Org. Chem. , vol.65 , pp. 1702-1706
- Fukuzawa, S.¹ Matsuzawa, H.² Yoshimitsu, S.³

42
- 35548982108
- Chena, X.; Zhang, C.; Wu, H.; Yu, X.; Su, W.; Cheng, J. Synthesis 2007, 3233-3239
- (2007) Synthesis , pp. 3233-3239
- Chena, X.¹ Zhang, C.² Wu, H.³ Yu, X.⁴ Su, W.⁵ Cheng, J.⁶

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