Asymmetric synthesis by the intramolecular haloetherification reaction of ene acetal: Discrimination of prochiral dienes in cyclohexane systems

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 8, 2005, Pages 952-957

  Fujioka, Hiromichi ^a   Kotoku, Naoyuki ^a   Sawama, Yoshinari ^a   Kitagawa, Hidetoshi ^a   Ohba, Yusuke ^a   Wang, Tsung Lung ^a   Nagatomi, Yasushi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

(+) hydrobenzoin; Cyclohexa 1,4 diene; Desymmetrization; Ene acetal; Intramolecular haloetherification

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; ALKADIENE; CYCLOHEXANE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; ETHERIFICATION; OXIDATION; STEREOCHEMISTRY;

ACETALS; CYCLOHEXANES; ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 24944437553     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.952     Document Type: Article

References (23)

1. Mikami K., Yoshida A., J. Synth. Org. Chem. Jpn., 60, 732-739 (2002).
2. Willis M. C., J. Chem. Soc., Perkin Trans. 1, 1999, 1765-1784 (1999).
3. Maganus S. R., Tetrahedron, 51, 2167-2213 (1995).
4. Poss C. S., Schreiber S. L., Acc. Chem. Res., 27, 9-17 (1994).
5. Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990).
6. Johnson C. R., Acc. Chem. Res., 31, 333-341 (1998).
7. Schoffers E., Golebiowski A., Johnson C. R., Tetrahedron, 52, 3769-3826 (1996).
8. Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., Chem. Rev., 92, 1071-1140 (1992).
9. Ohno M., Kobayashi S., Kurihara M., J. Synth. Org. Chem. Jpn., 44, 38-48 (1986).
10. Fujioka H., Kitagawa H., Matsunaga N., Nagatomi Y., Kita Y., Tetrahedron Lett., 37, 2245-2248 (1996).
11. Fujioka H., Kitagawa H., Nagatomi Y., Kita Y., J. Org. Chem., 61, 7309-7315 (1996).
12. Kitagawa O., Momose S., Fushimi Y., Taguchi T., Tetrahedron Lett., 40, 8827-8831 (1999).
13. Yokomatsu T., Iwasawa H., Shibuya S., Tetrahedron Lett., 33, 6999-7002 (1992).
14. Yokomatsu T., Iwasawa H., Shibuya S., J. Chem. Soc., Chem. Commun., 1992, 728-729 (1992).
15. Kitagawa O., Hanano T., Tanabe K., Shiro M., Taguchi T., J. Chem. Soc., Chem. Commun., 1992, 1005-1007 (1992).
16. Fuji K., Node M., Naniwa Y., Kawabata T., Tetrahedron Lett., 31, 3175-3178 (1990).
17. Hart D. J., Huang H.-C., Krishnamurthy R., Schwartz T., J. Am. Chem. Soc., 111, 7507-7519 (1989).
18. Takano S., Murakata C., Imamura Y., Tamura N., Ogasawara K., Heterocycles, 16, 1291-1294 (1981).
19. For the communication related to the similar concept, see: Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y., Tetrahedron Lett., 43, 4825-4828 (2002).
20. Scholz D., Schmidt U., Chem. Ber., 107, 2295-2298 (1974).
21. Wang Z.-M., Sharpless K. B., J. Org. Chem., 59, 8302-8303 (1994).
22. Marshall J. A., Wuts P. G. M., J. Org. Chem., 43, 1086-1089 (1978).
23. Mancuso A. J., Huang S. L., Swern D., J. Org. Chem., 43, 2480-2482 (1978).