4-(Arylsulfonyl)glycals in synthesis. Cation-mediated synthesis of 2,6- disubstituted dihydropyrans

Synlett

Volumn , Issue 1, 1999, Pages 132-134

  Bailey, Jennifer M ^a   Craig, Donald ^a   Gallagher, Peter T ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Cation mediated; Dihydropyran; Glycal; S(N)1'; Sulfone; Synthesis

Indexed keywords

DIHYDROPYRIDINE DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL BINDING; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032935562     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2540     Document Type: Article

References (20)

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2. Sarabia-García, F.; López-Herrera, F. J.; Pino-González, M. S. Tetrahedron Lett. 1994, 35, 6709-6712.
3. Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1995, 36, 5815-5818.
4. For related reactions of the vinylogous 2-(phenylsulfonyl) tetrahydro-2H-pyrans, see: Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
5. For recent studies of related reactions of glycal esters with organocopper and organozinc reagents, see: Thorn, S. N.; Gallagher, T. Synlett 1996, 856-858; Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861.
6. For recent studies of related reactions of glycal esters with organocopper and organozinc reagents, see: Thorn, S. N.; Gallagher, T. Synlett 1996, 856-858; Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861.
7. Taylor, E. C.; Chiang, C.-S. Synthesis 1977, 467.
8. Bonete, P.; Nájera, C. Tetrahedron 1995, 51, 2763-2776.
9. 13C nmr and ir spectra, and which showed low-resolution ms and either elemental combustion analysis or high-resolution ms characteristics in accord with the assigned structures.
10. Paquette, L. A.; Oplinger, J. A. J. Org. Chem. 1988, 53, 2953-2959.
11. We have not prepared isomerically pure samples of anti-9. We thank Professor David J. Williams and Dr Andrew J. P. White of this department for the X-ray crystallographic determinations.
12. Carreño, M. C.; González, M. P.; Ribagorda, M. J. Org. Chem. 1996, 61, 6758-6759.
13. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503-7509.
14. 2 (0.1M) at rt for 12 h followed by heating under reflux for 12 h gave 20% of [2R*,6S*]-6-methyl-2-phenyltetrahydropyran, together with 80% unreacted starting material. See: Van Tamelen, E. E.; Dewey, R. S.; Timmons, R. J. J. Am. Chem. Soc. 1961, 83, 3725-3726.
15. 14O requires C, 82.71; H, 8.09%).
16. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666.
17. 2 effected the conversion of 13 into 16. Samarium(II) iodide was similarly unreactive towards the acetate derivative from 13.
18. For recent examples of organocopper-mediated ring-opening reactions of glycal epoxides, see; Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem. Int. Ed. Engl. 1998, 37, 193-196.
19. +, 364.1572).
20. Yield based on recovery of 8% unreacted starting material.