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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 : (152)

References (81)
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    • 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.
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    • 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.
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    • 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.
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    • Doyle, M.P.1    Phillips, I.M.2    Hu, W.3
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    • 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
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    • 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.
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    • Liu, P.1    Jacobsen, E.N.2
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    • 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.
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    • 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.
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    • Wang, B.1    Feng, X.2    Huang, Y.3    Liu, H.4    Cui, X.5    Jiang, Y.6
  • 20
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    • 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
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    • 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.
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    • Du, H.1    Long, J.2    Hu, J.3    Li, X.4    Ding, K.5
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    • 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.
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    • Schaus, S.E.1    Brånalt, J.2    Jacobsen, E.N.3
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    • note
    • See Experimental Section.
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    • (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.
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    • (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.
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    • (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
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    • (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.
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    • 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.
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    • Kobayashi, S.1    Hachiya, I.2    Ishitani, H.3    Araki, M.4
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    • note
    • See Supporting Information.
  • 79
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    • See ref 26b
    • See ref 26b.
  • 80
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    • note
    • A similar intermediate which suggested the stepwise mechanism was also isolated in the reaction of benzaldehyde with 1h.
  • 81
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    • 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)).


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