Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8895-8898

  Tomooka, Katsuhiko ^a   Nagasawa, Atsushi ^a   Wei, Shih Yi ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ZARAGOZIC ACID A;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030566784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02077-1     Document Type: Article

References (24)

1. 1. Reviews: (a) Evans, D. A.;Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. Pure Appl. Chem. 1981, 53, 1109-1127. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
2. 1. Reviews: (a) Evans, D. A.;Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. Pure Appl. Chem. 1981, 53, 1109-1127. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
3. (b) Oppolzer, W. Tetrahedron 1987, 43, 1969-2004.
4. 2. This work was presented at the 69th Annual Meeting of the Chemical Society of Japan, Kyoto, 1995, 1H101. After the completion of this work, a conceptually similar but operationally different work has recently been reported by the Merck Frosst group: Black, W. C.; Giroux, A.; Greidanus, G. Tetrahedron Lett. 1996, 37, 4471-4474.
5. 3. (a) Krebs, E.-P. Helv. Chim. Acta 1981, 64, 1023-1025.
6. (b) Kende, A. S.; Toder, B. H. J. Org. Chem. 1982, 47, 163-167.
7. (c) Cameron, D. W.; Looney, M. G.; Pattermann, J. A. Tetrahedron Lett. 1995, 36, 7555-7558.
8. For mechanistic discussion: (d) Galatsis, P.; Manwell, J. J.; Millan, S. D. Tetrahedron Lett. 1996, 37, 5261-5264.
9. 4. Imides 1 and 2 were prepared from (E)-2- and (E)-3-pentenoyl chloride, respectively, via reactions with (25)-bornane-10,2-sultam or (4S)-isopropyl-2-oxazolidinone according to the reported procedures: Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772; Gage, J. R.; Evans, D. A. Org. Synth. Coll. 1993, VIII, 339-343.
10. 4. Imides 1 and 2 were prepared from (E)-2- and (E)-3-pentenoyl chloride, respectively, via reactions with (25)-bornane-10,2-sultam or (4S)-isopropyl-2-oxazolidinone according to the reported procedures: Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772; Gage, J. R.; Evans, D. A. Org. Synth. Coll. 1993, VIII, 339-343.
11. 3): the δ value (ppm) of α-CH, 3.70-3.80 (m) for (E, S)-3a, 4.08 (dddd, J=9.3, 8.4, 6.0, 0.9 Hz) for (Z, R)-3a, and 4.13 (dddd, J=9.3, 7.1, 7.1, 0.9 Hz) for (Z, S)-3a.
12. 6. The geometric and diastereomeric purity were determined by capillary GC (PEG 20M, 25m).
13. 3, 18.57 for (S)-4a and 18.72 for (R)-4a.
14. 8. Selected recent examples of 1,3-remote stereocontrol: (a) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1081-1084.
15. (b) White, J. D.; Johnson, A. T. J. Org. Chem. 1994, 59, 3347-3358.
16. (c) Ishiwata, H.; Sone, H.; Kigoshi, H.; Yamada, K. J. Org. Chem. 1994, 59, 4712-4713.
17. (d) Nagao, Y.; Inoue, T.; Hashimoto, K.; Hagiwara, Y.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1419-1420.
18. 9. Total synthesis of zaragozic acid A Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; Greca, S. L. Angew. Chem. Int. Ed. Engl. 1994, 33, 2190-2191. For the synthesis of the C6 side chain of zaragozic acid A: (a) Nicolaou, K. C.; Yue, E. D.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187.
19. 9. Total synthesis of zaragozic acid A Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; Greca, S. L. Angew. Chem. Int. Ed. Engl. 1994, 33, 2190-2191. For the synthesis of the C6 side chain of zaragozic acid A: (a) Nicolaou, K. C.; Yue, E. D.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187.
20. (b) Shlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331-1334.
21. w=0.049 (Fig.1). (equation presented) Fig. 1 ORTEP representation of 5
22. 8b
23. 3): the δ value (ppm) of β-CH, 6.80 for (4S, 6S)-7 and 6.87 for (4S, 6R)-7.
24. 14. Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T., the following paper.