Asymmetrization of a meso 1,2-enediol bis(trimethylsilyl) ether using a (S)-BINOL monoisopropyl ether(BINOL-Pr(i))-tin tetrachloride complex: An alternative route to (-)-ketodicyclopentadiene and (-)-ketotricyclononene

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6429-6432

  Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030862004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01488-3     Document Type: Article

References (18)

1. A review: Ogasawara, K. J. Synth. Org. Chem. Jpn. 1996, 54, 15 and references cited therein. Recent examples: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101. Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527 and references cited therein.
2. A review: Ogasawara, K. J. Synth. Org. Chem. Jpn. 1996, 54, 15 and references cited therein. Recent examples: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101. Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527 and references cited therein.
3. A review: Ogasawara, K. J. Synth. Org. Chem. Jpn. 1996, 54, 15 and references cited therein. Recent examples: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101. Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527 and references cited therein.
4. Taniguchi, T.; Goto, Y.; Ogasawara, K. Synlett 1997, 707.
5. Miller, R. D.; Dolce, D. L.; Merritt, V. Y. J. Org. Chem. 1976, 41, 1221.
6. (a) Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179.
7. (b) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
8. (c) Ishihara, K.; Nakamura, S.; Yamamoto, H. Croat. Chem. Acta 1996, 69, 513.
9. (d) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411.
10. Synthesis of a series of optically active BINOL monoalkyl ethers by the Mitsunobu reaction has been carried out by the present group: Takahashi, M.; Ogasawara, K. to be published.
11. iOH-hexane), was used in the present study.
12. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Org. Reactions 1992, 42, 335.
13. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Org. Reactions 1992, 42, 335.
14. Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359.
15. When acetylation of the acyloin (-)-5 was carried out with acetic anhydride in the presence of pyridine, some racemization (∼10%) occurred though the endo-acetate (-)-8 was obtained stereoselectively in good yield.
16. A pertinent monograph, see: Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
17. Yamane, T.; Takahashi, M.; Ogasawara, K. Synthesis 1995, 444.
18. We found that the racemic acyloin (±)-5 was kinetically resolved to give the optically active acetate (-)-8 in 50% yield with >99% ee leaving the unchanged optically active acyloin (+)-5 in 49% recovery with >99% ee: Taniguchi, T.; Ogasawara, K. Chem. Commun. in press.