Straightforward synthesis of α,β-epoxysilanes from terminal epoxides by lithium 2,2,6,6-tetramethylpiperidide-mediated deprotonation-in situ silylation

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7895-7897

  Hodgson, David M ^a   Reynolds, Nigel J ^a   Coote, Steven J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Epoxides; Lithiation; Silicon and compounds

Indexed keywords

EPOXIDE; LITHIUM 2,2,6,6 TETRAMETHYLPIPERIDIDE; LITHIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 0037190868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01893-2     Document Type: Article

References (23)

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11. 3SnCl) were unsuccessful.
12. 2, 20°C, 18 h (89%).
13. 2, 20°C, 18 h (89%).
14. 2, 20°C, 18 h (89%).
15. 2, 20°C, 18 h (89%).
16. 2, 20°C, 18 h (89%).
17. 2, 20°C, 18 h (89%).
18. 2, 20°C, 18 h (89%).
19. 3 requires 216.1599.
20. For other examples of the lack of reactivity of LTMP with disubstituted epoxides, see: (a) Yasuda, A.; Tanaka, S.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6513-6514; (b) Yasuda, A.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1705-1708.
21. For other examples of the lack of reactivity of LTMP with disubstituted epoxides, see: (a) Yasuda, A.; Tanaka, S.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6513-6514; (b) Yasuda, A.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1705-1708.
22. . For some examples of the conversion of α,β-epoxysilanes into useful products which retain a stereocentre from the starting α,β-epoxysilane, see: Jankowski P., Raubo P., Wicha J. Synlett. 1994;985-992.
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