A novel method for inside selective silylation of 1,2-diols

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2422-2423

  Tanino, Keiji ^a   Shimizu, Tadashi ^a   Kuwahara, Michio ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL;

ANALYTIC METHOD; ARTICLE; CHEMICAL BINDING; CHEMICAL MODIFICATION; DRUG SELECTIVITY; REACTION ANALYSIS; SILYLATION; SYNTHESIS;

EID: 0032540485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722358     Document Type: Article

References (22)

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11. Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206.
12. It has been reported that treatment of a dimethylsilylene derivative of a 1,3-diol with tert-butyllithium induced regioselective cleavage of the less hindered Si-O bond to yield the corresponding siloxy alcohol: Mukaiyama, T.; Shiina, I.; Kimura, K.; Akiyama, Y.; Iwadare, H. Chem. Lett. 1995, 229.
13. Dialkyl silylene derivatives of 1,2-diols are much less stable than those of 1,3-diols. See ref 11.
14. (a) Trost, B. M.; Caldwell, C. G. Tetrahedron Lett. 1981, 22, 4999.
15. (b) Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem. 1983, 48, 3252.
16. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871.
17. Treatment of 2-(butyldi-tert-butylsiloxy)-1-hexanol (1a) with tetrabutylammonium fluoride in THF at room temperature overnight effected smooth removal of the bulky silyl group.
18. The same product was also obtained by treating aldehyde 11 with methyllithium.
19. Treatment of the aldehyde with DIBAL afforded alcohol 6a, which was then converted into the corresponding MTPA ester. HPLC analysis of the MTPA ester indicated that the diastereomeric excess is >95%.
20. Diastereoselective intramolecular allylation reaction of a β-(allylsiloxy)aldehyde promoted by a Lewis arid has been reported: Reetz, M. T.; Jung, A.; Bolm, C. Tetrahedron 1988, 44, 3889.
21. It has been reported that the reaction of [2-trimethylsilyl)ethynyl]lithium and 2-(tert-butyldiphenylsiloxy)heptanal afforded the corresponding adduct as an 84:16 mixture of anti and syn isomers: Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L, Larchevêque, M. Synlett 1993, 217.
22. Crossover experiments were performed by using a 1:1 mixture of α-(alkynylsiloxy) aldehydes 12 and 13, and no product arising from an intermolecular addition reaction was observed. See the Supporting Information.