Dispiroketals in Synthesis (Part 20) 1: Preparation of Chiral 2,2′-Bis(halomethyl) and 2,2′-Bis(phenylthiomethyl)dihydropyrans

Synlett

Volumn 1996, Issue 8, 1996, Pages 787-788

  Ley, Steven V ^a   Mio, Shigeru ^a   Meseguer, Benjamin ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542711456     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5520     Document Type: Article

References (14)

1. Dispiroketals in Synthesis, Part 19: Downham, R.; Edwards, P, J.; Entwistle, D. A.; Hughes, A. B.; Kim, K. S.; Ley, S. V. Tetrahedron: Asymmery 1995, 6, 2403.
2. Ley, S. V.; Downham, R.; Edwards, P. J.; Innes, J, E.; Woods, M.; Comtemp. Org. Synth. 1995, 2, 365.
3. (a) Edwards, P. J.; Ley, S. V. Synlett. 1995, 898.
4. (b) Genicot, C.; Ley, S. V. Synthesis, 1994, 1275.
5. (c) Edwards, P. J.; Entwistle, D. A.; Genicot, C.; Kim, K. S.; Ley, S. V. Tetrahedron Lett. 1994, 35, 7443.
6. Edwards, P. J.; Entwistle, D. A.; Ley, S. V.; Owen, D. R.; Perry, E. J. Tetrahedron: Asymmetry 1994, 5, 553.
7. (a) Edwards, P. J.; Entwistle, D. A.; Genicot, C.; Ley, S. V.; Visentin, G. Tetrahedron: Asymmetry 1994, 5, 2609.
8. (b) Entwistle, D. A.; Hughes, A. B.; Ley, S. V.; Visentin, G. Tetrahedron Lett. 1994, 35, 777.
9. Kang, S-K.; Leon, J-H.; Yamaguchi, T.; Hong, R-K.; Ko, B-S. Tetrahedron: Asymmetry 1995, 6, 97.
10. 2 gas: 35psi; The column temperature was maintained at 75°C. The retention time of the (65)-isomer was 28.3min and the (6R)-ismoer 3 was 29.1 min.
11. Ley, S. V.; Leslie, R.; Tiffin, P. D.; Woods, M. Tetrahedron Lett. 1992, 33, 4767.
12. 13C-NMR. Also 8 includes ca. 4% of meso-compound, the effect of these contaminants is to lower the resulting enantiomeric excesses in later enantiodiscriminating reactions, see following papers. Ley, S. V.; Mio, S. Synlett 1996, 789. Ley, S. V.; Mio, S.; Meseguer, B. Synlett 1996, 791.
13. 13C-NMR. Also 8 includes ca. 4% of meso-compound, the effect of these contaminants is to lower the resulting enantiomeric excesses in later enantiodiscriminating reactions, see following papers. Ley, S. V.; Mio, S. Synlett 1996, 789. Ley, S. V.; Mio, S.; Meseguer, B. Synlett 1996, 791.
14. 3).