Stereodivergent Synthesis of Enantiopure Tetrahydropyrans via the Silyloxy-Cope Rearrangement of Chiral Aldol Products

Synlett

Volumn 1997, Issue 7, 1997, Pages 815-817

  Schneider, Christoph ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003112544     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5748     Document Type: Article

References (25)

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3. a) Edmunds, A. J. F.; Trueb, W. Tetrahedron Lett. 1997, 38, 1009-1012;
4. b) Smith, N. D.; Kocienski, P. J.; Street, S. D. A. Synthesis 1996, 652-665;
5. c) Banwell, M. G.; Bui, C. T.; Simpson, G. W.; Watson, K. G. J. Chem. Soc., Chem. Commun. 1996, 723-724;
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13. a) Schneider, C.; Rehfeuter, M. Synlett 1996, 212-214;
14. b) Schneider, C.; Rehfeuter, M. Tetrahedron 1997, 53, 133-144.
15. a) Black, W. C.; Giroux, A.; Greidanus, G. Tetrahedron Lett. 1996, 37, 4471-4474;
16. b) Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. ibid. 1996, 37, 8899-8900.
17. a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2128-2129;
18. b) Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron Lett. 1986, 27, 4957-4960.
19. Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404.
20. 13C NMR spectroscopy.
21. 3: 200.1412, found 200.1412. All new compounds were fully characterized by NMR, IR, MS, HRMS and/or combustion analysis.
22. -1. Structural refinement based on 3429 independently collected reflections. R1= 0.0269, wR2= 0.0738. The structure was solved with direct methods (SHELX90, Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467). The crystal data have been deposited with the Cambridge Crystallographic Data Centre and may be ordered from: The Director, CCDC, 12 Union Road, Cambridge, CB21EZ, UK.
23. a) Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138-141;
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25. The double bond configuration of enoates can also play a crucial role for the stereoselectivity of intramolecular conjugate additions leading to tetrahydropyrans, see: Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1996, 967.