Stereoselective methoxyselenenylation of acyclic allylic alcohol derivatives: A method for the synthesis of 1,3-anti-diols

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1249-1252

  Kim, Kwan Soo ^a   Park, Heung Bok ^a   Kim, Ji Young ^a   Ahn, Yeong Hee ^a   Jeong, In Howa ^b  

^a Yonsei University   (South Korea)

^b Yonsei University Wonju   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030065102     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02408-5     Document Type: Article

References (18)

1. For reviews, see: (a) Organoselenium Chemistry; Liotta, D. Ed.; John Wiley and Sons, Inc.: New York, 1987.
2. (b) Selenium Reagents and Intermediates in Organic Synthesis; Paulmier, C. Ed.; Pergamon Press: Oxford, 1986.
3. Ager, D. J.; East, M. B. Tetrahedron 1992, 48, 2803-2894.
4. Liotta, D.; Zima, G.; Saindane, M. J. Org. Chem. 1982, 47, 1258-1267.
5. Haughan, A. F.; Knight, J. R.; Sweeney, J. B. Tetrahedron Lett. 1994, 35, 1781-1784.
6. Cooper, M. A.; Ward, A. D. Tetrahedron Lett. 1995, 36, 2327-2330.
7. Barton, D. H. R.; Hall, M. B.; Lin, Z.; Parekh, S. I.; Reibenspies, J. J. Am. Chem. Soc. 1993, 115, 5056-5059.
8. Burling, F. T.; Goldstein, B. M. J. Am. Chem. Soc. 1992, 114, 2313-2320.
9. In the absence of DTBP, the reaction became less clean and the lower yield was observed. Temperature and solvent did not appreciably affect the stereochemistry and the yield, although the reaction time increased at lower temperature (0°C) or by using methylene chloride/ MeOH solution.
10. +, 1.3), 198 (5.8), 197 (5.7), 158 (2.6), 157 (10.2), 155 (5.5), 91 (100), 59 (5.3). All new compounds gave satisfactory spectroscopy and/or microanalytical data.
11. 3) δ 0.93 (t, J= 7.45 Hz, 3 H), 1.14 (d, J = 6.14 Hz, 3 H), 1.54-1.72 (m, 2 H), 3.27 (s, 3 H), 3.49-3.62 (m, 2 H), 4.45 and 4.60 (ABq, J = 11.5 Hz, 2 H), 7.25-7.36 (m, 5 H); MS (EI) m/z (rel intensity) 190 (7.6), 161 (14.0), 107 (12.8), 91 (100), 84 (26.6), 59 (16.1).
12. 3) δ 100.4, 68.3, 63.0, 40.0, 29.0, 25.2, 25.0, 21.8, 9.8; MS (EI) m/z (rel intensity) 143 (75.1), 83 (87.3), 59 (100), 43 (54.9).
13. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
14. 3) δ 0.85 (t, J = 7.42 Hz, 3 H), 1.46 (d, J = 7.15 Hz 3 H), 1.54-1.72 (m, 2 H), 2.06 (s, 3 H), 2.56 (brs, 1 H), 3.35 (dq, J = 7.15, 4.95 Hz, 1 H), 3.61-3.71 (m, 1 H), 4.99-5.07 (m, 1 H), 7.19-7.29 (m, 3 H), 7.47-7.60 (m, 2 H).
15. 3) δ 1.01 (t, J = 7.42 Hz, 6 H), 1.51-1.66 (m, 4 H), 3.45-3.54 (m, 2 H), 4.97 (s, 2 H).
16. Gu, Z. M.; Zeng, L.; Fang, X. P.; Colman-Saizarbitoria, T.; Huo, M.; McLaughlin, J. L. J. Org. Chem. 1994, 59, 5162-5172.
17. Exclusive generation of products through B-1 might also be explained by assuming the oxonium ion-like cyclic transition states. The cyclic transition states from B-1 forming oxonium ions 16 and 17 would be in the lower energy than those from B-2 forming the corresponding oxonium ions.
18. We observed the formation of intermediates, probably orthoesters 18 and 19, on TLC during the reaction but were unable to isolate them owing to their instability.