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Synlett

Volumn , Issue 17, 2007, Pages 2659-2662

New chiral hydroxyoxazolines based on ketopinic acid and their use in the asymmetric Diels-Alder reaction

(4) Barroso, Santiago a Blay, Gonzalo a Cardona, Luz a Pedro, José R a

a UNIVERSITY OF VALENCIA (Spain)

Author keywords

Alkenes; Asymmetric catalysis; Copper; Diels Alder reactions; Ligands

Indexed keywords

ACID; AMINOALCOHOL; COPPER; HYDROXYOXAZOLINE; KETOPINIC ACID; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; EPIMERIZATION;

EID: 35748944147 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991052 Document Type: Article

Times cited : (6)

References (38)

1
- 0003779363
- Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim
- (a) Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998.
- (1998) Transition Metals for Organic Synthesis

2
- 0003445429
- Jacobsen, E. N, Pfaltz, M, Yamamoto, H, Eds, Springer: Berlin
- (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, M.; Yamamoto, H., Eds.; Springer: Berlin, 1999.
- (1999) Comprehensive Asymmetric Catalysis

3
- 0003544583
- 2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim
- (c) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000.
- (2000) Catalytic Asymmetric Synthesis

4
- 0002032726
- 2-symmetric ligands, see: (a) Whitesell, J. Chem. Rev. 1989, 89, 1581.
- 2-symmetric ligands, see: (a) Whitesell, J. Chem. Rev. 1989, 89, 1581.

5
- 0032473520
- (b) Halm, C.; Kurth, M. J. Angew. Chem. Int. Ed. 1998, 37, 510.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 510
- Halm, C.¹ Kurth, M.J.²

6
- 35748941524
- 1-symmetric ligands, see: Humphries, A. C.; Pfaltz, A. In Stimulating Concepts in Chemistry; Vögtle, F.; Stoddart, J. F.; Shibashaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 89.
- 1-symmetric ligands, see: Humphries, A. C.; Pfaltz, A. In Stimulating Concepts in Chemistry; Vögtle, F.; Stoddart, J. F.; Shibashaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 89.

7
- 33749828310
- For a review on BOX-catalyzed reactions see
- For a review on BOX-catalyzed reactions see: Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561.
- (2006) Chem. Rev , vol.106 , pp. 3561
- Desimoni, G.¹ Faita, G.² Jørgensen, K.A.³

8
- 0002672006
- (a) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
- (1997) Chem. Commun , pp. 919
- Angell, R.M.¹ Barrett, A.G.M.² Braddock, D.C.³ Swallow, S.⁴ Vickery, B.D.⁵

9
- 0032518889
- (b) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261.
- (1998) Tetrahedron Lett , vol.39 , pp. 261
- Sagasser, I.¹ Helmchen, G.²

10
- 0002832598
- (c) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. J. Chem. Soc., Dalton Trans. 2000, 4432.
- (2000) J. Chem. Soc., Dalton Trans , pp. 4432
- Davenport, A.J.¹ Davies, D.L.² Fawcett, J.³ Garratt, S.A.⁴ Russell, D.R.⁵

11
- 0034724942
- (d) Chelucci, G.; Sanna, M. G.; Gladiali, S. Tetrahedron 2000, 56, 2889.
- (2000) Tetrahedron , vol.56 , pp. 2889
- Chelucci, G.¹ Sanna, M.G.² Gladiali, S.³

12
- 0035888914
- (e) Wu, X.-Y.; Xu, H.-D.; Tang, F.-Y.; Zhou, Q.-L. Tetrahedron: Asymmetry 2001, 12, 2565.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2565
- Wu, X.-Y.¹ Xu, H.-D.² Tang, F.-Y.³ Zhou, Q.-L.⁴

13
- 0043201045
- (f) Brunner, H.; Kagan, H.; Kreutzer, G. Tetrahedron: Asymmetry 2003, 14, 2177.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2177
- Brunner, H.¹ Kagan, H.² Kreutzer, G.³

14
- 17444375310
- (g) Västila, P.; Pastor, I. M.; Adolfsson, H. J. Org. Chem. 2005, 70, 2921.
- (2005) J. Org. Chem , vol.70 , pp. 2921
- Västila, P.¹ Pastor, I.M.² Adolfsson, H.³

15
- 18844397549
- (h) Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837.
- (2005) Org. Lett , vol.7 , pp. 1837
- Lee, J.-Y.¹ Miller, J.J.² Hamilton, S.S.³ Sigman, M.S.⁴

16
- 4544296110
- Bolm, C.; Zani, L.; Rudolph, J.; Schiffers, I. Synthesis 2004, 2173.
- (2004) Synthesis , pp. 2173
- Bolm, C.¹ Zani, L.² Rudolph, J.³ Schiffers, I.⁴

17
- 24644519263
- Bolm, C.; Schmidt, F.; Zani, L. Tetrahedron: Asymmetry 2005, 16, 1367.
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1367
- Bolm, C.¹ Schmidt, F.² Zani, L.³

18
- 0001128282
- (a) Chang, J.-W.; Jang, D.-P.; Uang, B.-J.; Liao, F.-L.; Wang, S.-L. Org. Lett. 1999, 1, 2061.
- (1999) Org. Lett , vol.1 , pp. 2061
- Chang, J.-W.¹ Jang, D.-P.² Uang, B.-J.³ Liao, F.-L.⁴ Wang, S.-L.⁵

19
- 0033605050
- (b) Li, X.; Yeung, C.-H.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1999, 10, 759.
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 759
- Li, X.¹ Yeung, C.-H.² Chan, A.S.C.³ Yang, T.-K.⁴

20
- 0033524811
- (c) Chen, C.-J.; Chu, Y.-Y.; Liao, Y.-Y.; Tsai, Z.-H.; Wang, C.-C.; Chen, K. Tetrahedron Lett. 1999, 40, 1141.
- (1999) Tetrahedron Lett , vol.40 , pp. 1141
- Chen, C.-J.¹ Chu, Y.-Y.² Liao, Y.-Y.³ Tsai, Z.-H.⁴ Wang, C.-C.⁵ Chen, K.⁶

21
- 0001260024
- (d) Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
- (2000) Org. Lett , vol.2 , pp. 729
- Yang, K.-S.¹ Chen, K.²

22
- 0042233658
- (e) Jang, D.-P.; Chang, J.-W.; Uang, B.-J. Org. Lett. 2001, 3, 983.
- (2001) Org. Lett , vol.3 , pp. 983
- Jang, D.-P.¹ Chang, J.-W.² Uang, B.-J.³

23
- 0035945798
- (f) Gilbertson, S. R.; Fu, C. Org. Lett. 2001, 3, 161.
- (2001) Org. Lett , vol.3 , pp. 161
- Gilbertson, S.R.¹ Fu, C.²

24
- 0035898868
- (g) Palomo, C.; Aizpurua, J. M.; Oiarbide, M.; García, J. M.; González, A.; Odriozola, I.; Linden, A. Tetrahedron Lett. 2001, 42, 4829.
- (2001) Tetrahedron Lett , vol.42 , pp. 4829
- Palomo, C.¹ Aizpurua, J.M.² Oiarbide, M.³ García, J.M.⁴ González, A.⁵ Odriozola, I.⁶ Linden, A.⁷

25
- 0037033432
- (h) Chang, C.-W.; Yang, C.-T.; Hwang, C.-D.; Uang, B.-J. Chem. Commun. 2002, 54.
- (2002) Chem. Commun , pp. 54
- Chang, C.-W.¹ Yang, C.-T.² Hwang, C.-D.³ Uang, B.-J.⁴

26
- 0000044772
- (i) Yang, K.-S.; Chen, K. Org. Lett. 2002, 4, 1107.
- (2002) Org. Lett , vol.4 , pp. 1107
- Yang, K.-S.¹ Chen, K.²

27
- 0037423177
- (j) Yang, K.-S.; Lee, W.-D.; Pan, J.-F.; Kwmin, C. J. Org. Chem. 2003, 68, 915.
- (2003) J. Org. Chem , vol.68 , pp. 915
- Yang, K.-S.¹ Lee, W.-D.² Pan, J.-F.³ Kwmin, C.⁴

28
- 3042743891
- (k) Bunlaksananusorn, T.; Knochel, P. J. Org. Chem. 2004, 69, 4595.
- (2004) J. Org. Chem , vol.69 , pp. 4595
- Bunlaksananusorn, T.¹ Knochel, P.²

29
- 15444372060
- (l) Hari, Y.; Aoyama, T. Synthesis 2005, 583.
- (2005) Synthesis , pp. 583
- Hari, Y.¹ Aoyama, T.²

30
- 29144520650
- (m) Chen, J.-H.; Venkatesham, U.; Lee, L.-C.; Chen, K. Tetrahedron 2006, 62, 887.
- (2006) Tetrahedron , vol.62 , pp. 887
- Chen, J.-H.¹ Venkatesham, U.² Lee, L.-C.³ Chen, K.⁴

31
- 35748982604
- 4: Bartlett, P. D.; Knox, L. H. Org. Synth., Coll. V; Wiley: New York, 1973, 689.
- 4: Bartlett, P. D.; Knox, L. H. Org. Synth., Coll. Vol. V; Wiley: New York, 1973, 689.

32
- 19544377371
- Sakakura, A.; Kondo, R.; Ishihara, K. Org. Lett. 2005, 7, 1971.
- (2005) Org. Lett , vol.7 , pp. 1971
- Sakakura, A.¹ Kondo, R.² Ishihara, K.³

33
- 0000097153
- Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
- (a) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 1177.
- (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177
- Evans, D.A.¹ Johnson, J.S.²

34
- 0003497902
- Kobayashi, S, Jørgensen, K. A, Eds, Wiley: New York
- (b) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley: New York, 2002.
- (2002) Cycloaddition Reactions in Organic Synthesis

35
- 0003441992
- Yamamoto, H, Ed, Wiley: New York
- (c) Lewis Acids in Organic Synthesis, Vol. 1; Yamamoto, H., Ed.; Wiley: New York, 2000.
- (2000) Lewis Acids in Organic Synthesis , vol.1

36
- 0003441992
- Yamamoto, H, Ed, Wiley: New York
- (d) Lewis Acids in Organic Synthesis, Vol. 2; Yamamoto, H., Ed.; Wiley: New York, 2000.
- (2000) Lewis Acids in Organic Synthesis , vol.2

37
- 0033603850
- Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 7582
- Evans, D.A.¹ Barnes, D.M.² Johnson, J.S.³ Lectka, T.⁴ von Matt, P.⁵ Miller, S.J.⁶ Murry, J.A.⁷ Norcross, R.D.⁸ Shaughnessy, E.A.⁹ Campos, K.R.¹⁰

38
- 35748960702
- Experimental Procedure for the Synthesis of Compound 2d: A solution of (S, )-ketopinic acid (1, 1.0 g, 5.5 mmol) in SOCl2 (4.5 mL) was refluxed for 2 h and the excess SOCl2 was removed under reduced pressure. The residue dissolved in CH 2Cl2 (3.8 mL) was added dropwise to a solution of (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol (3d, 0.82 g, 5.5 mmol) and Et3N (0.75 mL, 5.5 mmol) in CH2Cl 2 (3 mL) at 0°C under nitrogen. After 1 h, the mixture was diluted with EtOAc (150 mL, washed with 2 M HCl (2 x 30 mL, sat. aq NaHCO 3 (2 x 30 mL) and brine (30 mL, dried over MgSO4 and concentrated. The crude product was crystallized from hexane-CH 2Cl2 to give 4d; yield: 2.0 g (80, mp 163-165°C; [α]D25 +28.5 (c, 0.69, CHCl3, 1H NMR 300 MHz, CDCl3
- 2 to give 4d; yield: 2.0 g (80%);(...)

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