The formation of a peracetal and trioxane from an enol ether with copper(II) triflate and oxygen: Unexpected oxygenation of aldol intermediates

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2363-2366

  Vonwiller, Simone C ^b   Warner, Jacqueline A ^b   Mann, Simon T ^b   Haynes, Richard K ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; DIOXANE DERIVATIVE; KETONE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592557     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00349-3     Document Type: Article

References (22)

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3. 2. Haynes, R. K.; Vonwiller, J. Chem. Soc., Chem. Commun. 1990, 451.; Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
4. 2. Haynes, R. K.; Vonwiller, J. Chem. Soc., Chem. Commun. 1990, 451.; Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
5. 3. Jefford, C. W.; Kohmoto, S.; Boukouvalas, J.; Burger, U. J. Am. Chem. Soc. 1983, 105, 6498; Jefford, C. W.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1983, 66, 2615; Jefford, C. W.; Grant, H. G.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1984, 67, 2210.
6. 3. Jefford, C. W.; Kohmoto, S.; Boukouvalas, J.; Burger, U. J. Am. Chem. Soc. 1983, 105, 6498; Jefford, C. W.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1983, 66, 2615; Jefford, C. W.; Grant, H. G.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1984, 67, 2210.
7. 3. Jefford, C. W.; Kohmoto, S.; Boukouvalas, J.; Burger, U. J. Am. Chem. Soc. 1983, 105, 6498; Jefford, C. W.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1983, 66, 2615; Jefford, C. W.; Grant, H. G.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. Helv. Chim. Acta 1984, 67, 2210.
8. 4. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1989, 30, 485.
9. 4. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1989, 30, 485.
10. 5. Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 489; Lopez, L.; Troisi, L. Tetrahedron 1992, 35, 7321.
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13. 5 and stored under nitrogen over 4Å molecular sieves. All oxygenation experiments were carried out with 0.5-1 mmol of substrate in MeCN (0.06-0.08 M).
14. 8. The same result was obtained with the separated (E)-or (Z)-isomers of 7.
15. 3), 1.30-1.41 (1H, m), 1.47-1.53 (2H, m), 1.78-1.77 (4H, m), 1.59-1.93 (1H, br s, OH), 1.86-2.02 (3H, m), 3.00-3.11 (1H, m, H3a), 9.79 (1H, s, CHO). Preirradiation at δ 1.27 enhanced δ 1.86-2.02 (0.9%), and 9.79 (0.1%). nOe's: Preirradiation at δ 3.06 enhanced δ 1.47-1.53 (2.2%), 1.57-1.61 (1.0%), and 1.78-2.02 (4.9%). Preirradiation at δ 9.79 enhanced δ 3.00-3.11 (2.4%), and 1.95-2.02 (3.4%).
16. 10. Posner, G. H.; Oh, C. H.; Milhous, W. K. Tetrahedron Lett. 1991, 32, 4235.
17. 11. Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 843; Nelson, I. V.; Carson, R. C.; Iwamoto, R. T. J. Inorg. Nucl. Chem. 1961, 22, 279.
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19. 12. Schmittel, M. Top. Curr. Chem. 1994, 184.
20. 13. In certain intermolecular examples oxygenation to give trioxanes proceeds smoothly: Vonwiller, S. C.; Haynes, R. K. unpublished results.
21. 14. A relevant case is the oxygenation with triplet oxygen of a potassium enolate generated by an oxyanionic Cope rearrangement: Paquette, L. A.; DeRussy, D. T.; Pegg, N. A. ; Taylor, R. T.; Zydowsky, T. M. J. Org. Chem. 1989, 54, 4576.
22. 15. We are unaware of any study involving retroaldolisation which relates geometry to facility of cleavage.