Remote asymmetric induction for chiral 1,4-diols using a chiral acetal derived from chiral hydrobenzoin

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2245-2248

  Fujioka, Hiromichi ^a   Kitagawa, Hidetoshi ^a   Matsunaga, Naoki ^a   Nagatomi, Yasushi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029885657     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00266-3     Document Type: Article

References (28)

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9. (g) Zhang, H. -C.; Cosfanzo, M. Z.; Marganoff, B. Z. Tetrahedron Lett. 1994, 35, 4891.
10. 2-symmetric acetals, see: (a) Fujioka, H.; Kitagawa, H.; Yamanaka, T.; Kita, Y. Chem. Pharm. Bull 1992, 40, 3118.
11. (b) Fujioka, H.; Annoura, H.; Murano, K.; Kita, Y.; Tamura, Y. Chem. Pharm. Bull. 1989, 37, 2047 and references therein.
12. 2-symmetric acetals, see: (a) A. Alexakis and P. Mangeny, Tetrahedron: Asymmetry, 1990, 1, 477.
13. (b) H. Fujioka and Y. Kita, "Studies in Natural Product Chemistry", ed by Atta-ur-Rahman, Elsevier, Amsterdam, 1994; Vol 14, pp 469.
14. Chiral hydrobenzoin is readily available in both enantiomeric forms by asymmetric synthesis or resolution; for asymmetric synthesis, see, Wang, Z. -M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302, and for resolution of dl-hydrobenzoin, see "Optical Resolution Procedures for Chemical Compounds" ed by P. Mewman, Optical Information Center, Manhattan College, Riverdale, New York, 1984, Vol. 3, pp 353.
15. Chiral hydrobenzoin is readily available in both enantiomeric forms by asymmetric synthesis or resolution; for asymmetric synthesis, see, Wang, Z. -M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302, and for resolution of dl-hydrobenzoin, see "Optical Resolution Procedures for Chemical Compounds" ed by P. Mewman, Optical Information Center, Manhattan College, Riverdale, New York, 1984, Vol. 3, pp 353.
16. 4) is often used in halolactonization. Preparation: Lemieux, R. U.; Morgan, A. R. Can. J. Chem. 1965, 43, 2190.
17. For studies of halonium ion mediated neighboring group activation of acetal cleavage, see: (a) Robert, M.; Udodong, U. E.; Roberts, C.; Mootoo, D. R.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 1554.
18. (b) Roberts, C.; Madsen, R.; Fraser-Reid, B. . J. Am. Chem. Soc. 1995, 117, 1546.
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20. (d) Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, J.; Merritt, J. R.; Rao, C. S.; Roberts, C. Synlett 1992, 927.
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22. (f) Elvey, S. P.; Mootoo, D. R. J. Am. Chem. Soc. 1992, 60, 9685.
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24. (h) Mootoo, D. R.; Date, V. Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1987, 1462. References e-h include the reactions of remote stereocontrol.
25. The high stereoselectivity in the alcohol displacement reactions (a>b, c>d, see Table 1) might be assumed to favor the direct SN2-type reaction from bicyclic ion.
26. 4 reduction, and 3) hydrogenolysis.
27. The reason is not clear yet, but the preference of transition state B might be due to the repulsion between the halomethyl substituent and the anion species which might exist on the convex side of the cation.
28. For the reaction of a Grignard reagent and an acetal, see: Yuan, T. -M.; Yeh, S. -M.; Hsieh, Y. -T.; Luh, T. -Y. J. Org. Chem. 1994, 59, 8192 and references therein.