메뉴 건너뛰기




Volumn 125, Issue 13, 2003, Pages 3793-3798

Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-prelactone C and (+)-9-deoxygoniopypyrone

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL COMPOUNDS; ENANTIOSELECTIVITY;

EID: 0037414319     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028186k     Document Type: Article
Times cited : (153)

References (81)
  • 3
    • 0000884707 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • (c) Boger, D. L. In Comprehensive Organic Synthesis: Trost, B. M., Ed.; Pergamon Press: Oxford. 1991; Vol. 5, p 451.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 451
    • Boger, D.L.1
  • 6
    • 0000936493 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (1998) J. Org. Chem. , vol.63 , pp. 403
    • Schaus, S.E.1    Brånalt, J.2    Jacobsen, E.N.3
  • 7
    • 0033549737 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2398
    • Dossetter, A.G.1    Jamison, T.F.2    Jacobsen, E.N.3
  • 8
    • 0033982977 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2000) Chem.-Eur. J. , vol.6 , pp. 123
    • Simonsen, K.B.1    Svenstrup, N.2    Roberson, M.3    Jørgensen, K.A.4
  • 9
    • 0034163402 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2000) Heterocycles , vol.52 , pp. 1041
    • Yamada, T.1    Kezuka, S.2    Mita, T.3    Ikeno, T.4
  • 10
    • 0343022339 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5043
    • Leveque, L.1    Le Blanc, M.2    Pastor, R.3
  • 11
    • 0034339610 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2000) Chem. Lett. , pp. 824
    • Kezuka, S.1    Mita, T.2    Ohtsuki, N.3    Ikeno, T.4    Yamada, T.5
  • 12
    • 0035101858 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) Heterocvcles , vol.54 , pp. 395
    • Mihara, J.1    Aikawa, K.2    Uchida, T.3    Irie, R.4    Katsuki, T.5
  • 13
    • 0035961115 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) Tetrahedron , vol.57 , pp. 845
    • Aikawa, K.1    Irie, R.2    Katsuki, T.3
  • 14
    • 0034811817 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5366
    • Doyle, M.P.1    Phillips, I.M.2    Hu, W.3
  • 15
    • 0035904404 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9974
    • Thompson, C.F.1    Jamison, T.F.2    Jacobsen, E.N.3
  • 16
    • 0035980401 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10772
    • Liu, P.1    Jacobsen, E.N.2
  • 17
    • 0034860509 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2001) Bull. Chem. Soc. Jpn. , vol.74 , pp. 1333
    • Kezuka, S.1    Mita, T.2    Ohtsuki, N.3    Ikeno, T.4    Yamada, T.5
  • 18
    • 0037045239 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10
    • Long, J.1    Hu, J.2    Shen, X.3    Ji, B.4    Ding, K.5
  • 19
    • 0037023468 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) J. Org. Chem. , vol.67 , pp. 2175
    • Wang, B.1    Feng, X.2    Huang, Y.3    Liu, H.4    Cui, X.5    Jiang, Y.6
  • 20
    • 0036276134 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) Synlett , pp. 931
    • Kii, S.1    Hashimoto, T.2    Maruoka, K.3
  • 21
    • 0013263752 scopus 로고    scopus 로고
    • For a recent review of catalytic asymmetric HDA reactions of aldehydes involving Danishefsky's diene and its analogues, see ref 1e; for recent reports, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398. (c) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (d) Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041. (e) Leveque, L.; Le Blanc, M.; Pastor, R. Tetrahedron Lett. 2000, 41, 5043. (f) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno. T.; Yamada, T. Chem. Lett. 2000. 824. (g) Mihara, J.; Aikawa, K.; Uchida, T.; Irie, R.; Katsuki, T. Heterocvcles 2001, 54, 395. (h) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974. (k) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772. (l) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333. (m) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10. (n) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175. (o) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931. (p) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) Org. Lett. , vol.4 , pp. 4349
    • Du, H.1    Long, J.2    Hu, J.3    Li, X.4    Ding, K.5
  • 43
    • 0000936493 scopus 로고    scopus 로고
    • tert-Butyl methyl ether was used as an efficient solvent in asymmetric HDA reactions previously. See: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
    • (1998) J. Org. Chem. , vol.63 , pp. 403
    • Schaus, S.E.1    Brånalt, J.2    Jacobsen, E.N.3
  • 55
    • 0242612734 scopus 로고    scopus 로고
    • note
    • See Experimental Section.
  • 56
    • 0027475370 scopus 로고
    • (a) Bindseil, K. U.; Zeeck, A. Helv. Chim. Acta 1993, 76, 150. (b) Boddien, C.; Gerber-Nolte, J.; Zeeck, A. Liebigs Ann. 1996, 1381. Asymmetric total synthesis of (+)-Prelactone C has already been reported. However, in every case, many reaction steps were required. See: (c) Esumi, T.; Fukuyama, H.; Oribe, R.; Kawazoe, K.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1997, 38, 4823. (d) Chakraborty, T. K.; Tapadar, S. Tetrahedron Lett. 2001, 42, 1375.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 150
    • Bindseil, K.U.1    Zeeck, A.2
  • 57
    • 0006134014 scopus 로고    scopus 로고
    • (a) Bindseil, K. U.; Zeeck, A. Helv. Chim. Acta 1993, 76, 150. (b) Boddien, C.; Gerber-Nolte, J.; Zeeck, A. Liebigs Ann. 1996, 1381. Asymmetric total synthesis of (+)-Prelactone C has already been reported. However, in every case, many reaction steps were required. See: (c) Esumi, T.; Fukuyama, H.; Oribe, R.; Kawazoe, K.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1997, 38, 4823. (d) Chakraborty, T. K.; Tapadar, S. Tetrahedron Lett. 2001, 42, 1375.
    • (1996) Liebigs Ann. , pp. 1381
    • Boddien, C.1    Gerber-Nolte, J.2    Zeeck, A.3
  • 58
    • 0030947378 scopus 로고    scopus 로고
    • (a) Bindseil, K. U.; Zeeck, A. Helv. Chim. Acta 1993, 76, 150. (b) Boddien, C.; Gerber-Nolte, J.; Zeeck, A. Liebigs Ann. 1996, 1381. Asymmetric total synthesis of (+)-Prelactone C has already been reported. However, in every case, many reaction steps were required. See: (c) Esumi, T.; Fukuyama, H.; Oribe, R.; Kawazoe, K.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1997, 38, 4823. (d) Chakraborty, T. K.; Tapadar, S. Tetrahedron Lett. 2001, 42, 1375.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4823
    • Esumi, T.1    Fukuyama, H.2    Oribe, R.3    Kawazoe, K.4    Iwabuchi, Y.5    Irie, H.6    Hatakeyama, S.7
  • 59
    • 0035847461 scopus 로고    scopus 로고
    • (a) Bindseil, K. U.; Zeeck, A. Helv. Chim. Acta 1993, 76, 150. (b) Boddien, C.; Gerber-Nolte, J.; Zeeck, A. Liebigs Ann. 1996, 1381. Asymmetric total synthesis of (+)-Prelactone C has already been reported. However, in every case, many reaction steps were required. See: (c) Esumi, T.; Fukuyama, H.; Oribe, R.; Kawazoe, K.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1997, 38, 4823. (d) Chakraborty, T. K.; Tapadar, S. Tetrahedron Lett. 2001, 42, 1375.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1375
    • Chakraborty, T.K.1    Tapadar, S.2
  • 74
    • 85011648851 scopus 로고
    • Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472. To the best of our knowledge, this is the first example of the Michael reaction of silicon enolates with pyranone derivatives using a catalytic amount of a Lewis acid.
    • (1993) Synlett , pp. 472
    • Kobayashi, S.1    Hachiya, I.2    Ishitani, H.3    Araki, M.4
  • 76
    • 0242612731 scopus 로고    scopus 로고
    • note
    • See Supporting Information.
  • 79
    • 0242612732 scopus 로고    scopus 로고
    • See ref 26b
    • See ref 26b.
  • 80
    • 0242696839 scopus 로고    scopus 로고
    • note
    • A similar intermediate which suggested the stepwise mechanism was also isolated in the reaction of benzaldehyde with 1h.
  • 81
    • 0242444475 scopus 로고    scopus 로고
    • note
    • 2O (20 mol %), the aldol reaction of benzaldehyde with(Z)-2-benzyloxy-1-phenoxy-1-trimethylsiloxyethene proceeded in toluene′BuOMe at -20 °C to afford the corresponding syn-aldol adduct in high yield with high stereoselectivity (quantitative yield, syn/anti = > 30/1, 97% ee (syn)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.