Heterocyclic synthesis by C-C bond formation. Tetrahydrofuran and tetrahydropyran synthesis via oxonium ion-mediated cyclisation reactions

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8599-8602

  Craig, Donald ^a   King, N Paul ^a   Shaw, Antony N ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ALKYLATION; ARTICLE; CONFORMATION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030693926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10294-5     Document Type: Article

References (12)

1. Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1993, 34, 8539-8542.
2. For a review of cation-mediated routes to heterocycles using C-C bond-forming strategies, see: Overman, L. E. Aldrichimica Acta 1995, 28, 107-120.
3. 13C nmr, ir, and elemental combustion analysis and/or high-resolution ms characteristics in accord with the proposed structures.
4. 9) are after a single starting material recovery-recycle sequence.
5. Bates, F. X.; Donnelly, J. A.; Keegan, J. R. Tetrahedron 1991, 47, 4991-5000.
6. Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529-6530.
7. 13) gave identical diastereomer ratios in the cyclisation reaction.
8. 3OH.
9. 9. We thank Professor David J. Williams and Dr Andrew J. P. White for the X-ray structure determinations.
10. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
11. Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835-838, and references cited therein.
12. Craig, D.; Tierney, J. P.; Williamson, C. Tetrahedron Lett. 1997, 38, 4153-4156.