Regioselective and divergent opening of vinyl epoxides with ethoxyacetylene

Chemical Communications

Volumn , Issue 18, 2004, Pages 2086-2087

  Restorp, Per ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETYLENE DERIVATIVE; EPOXIDE; ETHOXYACETYLENE; ETHOXYACETYLIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL EPOXIDE DERIVATIVE;

ADDITION REACTION; ALKYLATION; ALKYNYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS ISOMER; CONSENSUS; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TRANS ISOMER;

EID: 6344238803     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408610d     Document Type: Article

References (25)

1. (a) J. M. Klunder and G. H. Posner, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, vol. 3;
2. (b) D. W. Knight, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, vol. 3;
3. (c) P. J. Garratt, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, vol. 3;
4. (d) J. Gorzynski, Synthesis, 1984, 629.
5. C. Jaime, R. M. Ortuno and J. Font, J. Org. Chem., 1987, 53, 139.
6. A. B. Smith III, S. M. Pitram, M. J. Gaunt and S. A. Kozmin, J. Am. Chem. Soc., 2002, 124, 14516.
7. (a) S. Hanessian, Aldrichim. Acta, 1989, 22, 3;
8. (b) for applications in total synthesis, see: S. Hanessian, in Total Synthesis of Natural Products: The Chiron Approach, ed. J. E. Baldwin, Pergamon, Oxford, 1983, vol. 3.
9. N. Krause and D. Seebach, Chem. Ber., 1988, 121, 1315.
10. A. Alexakis, E. Vrancken, P. Mangeney and F. Chemla, J. Chem. Soc., Perkin Trans. 1, 2000, 3352.
11. Synthesis of 1a-f were based on: (a) S. Hu, S. Jayamaran and A. C. Oehleschlager, J. Org. Chem., 1996, 61, 7513;
12. (b) D. Diez-Martin, N. R. Kotecha, S. V. Ley, S. Mantegani, J. C. Menedez, H. M. Osbourn and J. B. Banks, Tetrahedron, 1992, 48, 7899.
13. J. A. Marshall, Chem. Rev., 1989, 89, 1503.
14. (a) P. Shanmugan and M. Miyashita, Org. Lett., 2003, 5, 3265;
15. (b) M. Sasaki, K. Tanino and M. Miyashita, Org. Lett., 2001, 3, 1765.
16. R. B. Layton and J. Hooz, J. Am. Chem. Soc., 1971, 93, 7320.
17. N2′ alkynylation of vinyl epoxides has been reported affording the corresponding adduct in poor yield, see: F. Narjes and E. Schaumann, Justus Liebigs Ann. Chem., 1993, 841.
18. U. M. Lindstrom and P. Somfai, Synthesis, 1998, 109.
19. L. Liang, M. Ramaseshan and D. I. MaGee, Tetrahedron Lett., 1993, 49, 2159.
20. For a related reaction to form δ-lactones see: M. Movassaghi and E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 2456.
21. Lactone 15 was desilylated (TBAF, 97%) and the spectral data of the obtained alcohol was compared with literature data, see: U. Nubbemeyer, Synthesis, 1998, 1120.
22. G. Stork, T. Takahashi, I. Kawamoto and T. Suzuki, J. Am. Chem. Soc., 1978, 100, 8272.
23. (S,S)-15 was synthesized from enantiomerically pure vinyl epoxide 1a, see: A. Romero and C. Wong, J. Org. Chem., 2000, 65, 8264.
24. A. K. Chatterjee, T. L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360.
25. For preparation, see: L. D. Corey, S. M. Singh and A. C. Oehleschlager, Can. J. Chem., 1987, 65, 1821.