Highly enantioselective Hetero-Diels - Alder reaction of Brassard diene with aromatic aldehydes

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2185-2188

  Fan, Qian ^a   Lin, Lili ^a   Liu, Jie ^a   Huang, Yaozong ^a   Feng, Xiaoming ^a   Zhang, Guolin ^b  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; LACTONE DERIVATIVE; SCHIFF BASE; TITANIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 3142774263     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049364c     Document Type: Article

References (51)

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13. For some recent works on the hetero-Diels - Alder reaction, see: (a) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498. (b) Audrain, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487. (c) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404. (d) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793. (e) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221. (f) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563. (g) Joly, G. D.; Jacobsen, E. N.; Org. Lett. 2002, 4, 1795. (h) Du, H.-F.; Ding, K.-L. Org. Lett. 2003, 5, 1091. (i) Long, J.; Hu, J.-Y.; Shen, X.-Q.; Ji, B.-M.; Ding, K.-L. J. Am. Chem, Soc. 2002, 124, 10. (j) Yuan, Y.; Li, X.; Ding, K.-L. Org. Lett. 2002, 4, 3309. (k) Wang, B.; Feng, X.-M.; Cui, X.; Liu, H.; Jiang, Y.-Z. Chem. Commun. 2002, 1605. (1) Wang, B.; Feng, X.-M.; Huang, Y.-Z.; Liu, H.; Cui, X.; Jiang, Y.-Z. J. Org. Chem. 2002, 67, 2175. (m) Huang, Y.-Z.; Feng, X.-M.; Wang, B.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 2122.
14. For some recent works on the hetero-Diels - Alder reaction, see: (a) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498. (b) Audrain, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487. (c) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404. (d) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793. (e) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221. (f) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563. (g) Joly, G. D.; Jacobsen, E. N.; Org. Lett. 2002, 4, 1795. (h) Du, H.-F.; Ding, K.-L. Org. Lett. 2003, 5, 1091. (i) Long, J.; Hu, J.-Y.; Shen, X.-Q.; Ji, B.-M.; Ding, K.-L. J. Am. Chem, Soc. 2002, 124, 10. (j) Yuan, Y.; Li, X.; Ding, K.-L. Org. Lett. 2002, 4, 3309. (k) Wang, B.; Feng, X.-M.; Cui, X.; Liu, H.; Jiang, Y.-Z. Chem. Commun. 2002, 1605. (1) Wang, B.; Feng, X.-M.; Huang, Y.-Z.; Liu, H.; Cui, X.; Jiang, Y.-Z. J. Org. Chem. 2002, 67, 2175. (m) Huang, Y.-Z.; Feng, X.-M.; Wang, B.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 2122.
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16. For some recent works on the hetero-Diels - Alder reaction, see: (a) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498. (b) Audrain, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487. (c) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404. (d) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793. (e) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221. (f) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563. (g) Joly, G. D.; Jacobsen, E. N.; Org. Lett. 2002, 4, 1795. (h) Du, H.-F.; Ding, K.-L. Org. Lett. 2003, 5, 1091. (i) Long, J.; Hu, J.-Y.; Shen, X.-Q.; Ji, B.-M.; Ding, K.-L. J. Am. Chem, Soc. 2002, 124, 10. (j) Yuan, Y.; Li, X.; Ding, K.-L. Org. Lett. 2002, 4, 3309. (k) Wang, B.; Feng, X.-M.; Cui, X.; Liu, H.; Jiang, Y.-Z. Chem. Commun. 2002, 1605. (1) Wang, B.; Feng, X.-M.; Huang, Y.-Z.; Liu, H.; Cui, X.; Jiang, Y.-Z. J. Org. Chem. 2002, 67, 2175. (m) Huang, Y.-Z.; Feng, X.-M.; Wang, B.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 2122.
17. For some recent works on the hetero-Diels - Alder reaction, see: (a) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498. (b) Audrain, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487. (c) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404. (d) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793. (e) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221. (f) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563. (g) Joly, G. D.; Jacobsen, E. N.; Org. Lett. 2002, 4, 1795. (h) Du, H.-F.; Ding, K.-L. Org. Lett. 2003, 5, 1091. (i) Long, J.; Hu, J.-Y.; Shen, X.-Q.; Ji, B.-M.; Ding, K.-L. J. Am. Chem, Soc. 2002, 124, 10. (j) Yuan, Y.; Li, X.; Ding, K.-L. Org. Lett. 2002, 4, 3309. (k) Wang, B.; Feng, X.-M.; Cui, X.; Liu, H.; Jiang, Y.-Z. Chem. Commun. 2002, 1605. (1) Wang, B.; Feng, X.-M.; Huang, Y.-Z.; Liu, H.; Cui, X.; Jiang, Y.-Z. J. Org. Chem. 2002, 67, 2175. (m) Huang, Y.-Z.; Feng, X.-M.; Wang, B.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 2122.
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23. For some recent works on the syntheses of δ-lactones, see: (a) Mulzer, J.; Öhler, E. Chem. Rev. 2003, 103, 3753. (b) N'Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769. (c) Chakraborty, T. K.; Tapadar, S.; Tetrahedron Lett. 2003, 44, 2541. (d) Hanefeld, U.; Hooper, A. M.; Stauton, J. Synthesis 1999, 401. (e) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (f) Audrain, H.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 11543.
24. For some recent works on the syntheses of δ-lactones, see: (a) Mulzer, J.; Öhler, E. Chem. Rev. 2003, 103, 3753. (b) N'Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769. (c) Chakraborty, T. K.; Tapadar, S.; Tetrahedron Lett. 2003, 44, 2541. (d) Hanefeld, U.; Hooper, A. M.; Stauton, J. Synthesis 1999, 401. (e) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (f) Audrain, H.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 11543.
25. For some recent works on the syntheses of δ-lactones, see: (a) Mulzer, J.; Öhler, E. Chem. Rev. 2003, 103, 3753. (b) N'Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769. (c) Chakraborty, T. K.; Tapadar, S.; Tetrahedron Lett. 2003, 44, 2541. (d) Hanefeld, U.; Hooper, A. M.; Stauton, J. Synthesis 1999, 401. (e) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (f) Audrain, H.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 11543.
26. For some recent works on the syntheses of δ-lactones, see: (a) Mulzer, J.; Öhler, E. Chem. Rev. 2003, 103, 3753. (b) N'Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769. (c) Chakraborty, T. K.; Tapadar, S.; Tetrahedron Lett. 2003, 44, 2541. (d) Hanefeld, U.; Hooper, A. M.; Stauton, J. Synthesis 1999, 401. (e) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (f) Audrain, H.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 11543.
27. For some recent works on the syntheses of δ-lactones, see: (a) Mulzer, J.; Öhler, E. Chem. Rev. 2003, 103, 3753. (b) N'Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769. (c) Chakraborty, T. K.; Tapadar, S.; Tetrahedron Lett. 2003, 44, 2541. (d) Hanefeld, U.; Hooper, A. M.; Stauton, J. Synthesis 1999, 401. (e) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (f) Audrain, H.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 11543.
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34. (f) Pierres, C.; George, P.; Hijfte, L.; Ducep, J.-B.; Hibert, M.; Mann, A. Tetrahedron Lett. 2003, 44, 3645.
35. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
36. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
37. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
38. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
39. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
40. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
41. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
42. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
43. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
44. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
45. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
46. Some BINOL derivatives in HDA reaction: (a) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Gao, Q.-Z.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. Some chiral bisoxazolines in HDA reaction: (f) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582 and references therein, (g) Audrian, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487 and references therein. Some Schiff base ligands in HDA reaction: (h) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059. (j) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882. (k) Yuan, Y.; Long, J.; Sun, J.; Ding, K.-L. Chem. Eur. J. 2002, 8, 5033. (l) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
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