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Volumn 19, Issue 33, 1978, Pages 3043-3046

Chemistry of organosilicon compounds 113 chemoselective allylation of carbonyl compounds with allylsilanes promoted by tetra-n-butylammonium fluoride. A new synthesis of homoallyl alcohols

(3) Hosomi, Akira a Shirahata, Akibiko a Sakurai, Hideki a

a TOHOKU UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000174207 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)94934-2 Document Type: Article

Times cited : (196)

References (21)

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- and references cited therin
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11
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- a value of propene, a conjugate acid of allyl anion, is 36.5.

12
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- 2; n=1,2) react with alcohols by stepwise replacement of R and H with alkoxide in the presence of tetramethylammonium fluoride., Chem. Abstr. 83 1975 147538d
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13
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- Stanberry¹ Darmon² Fry³ Lenox⁴

16
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- By the Girgnard reaction with benzophenone, we found that the allylation occurred only at the tertiary site of the allylic part to give 3,3-dimethyl-4,4-diphenyl-but-l-ene-4-ol in 98 % yield.

17
- 84917986862
- It was found that the first step in this allylation was reversible (Scheme 1), and, therefore, that a sterically less hindered allylsilane around the silicon atom was obtained at the end of the reaction, when a mixture of regioisomers of alkyl-substituted allylsilanes was heated with stirring in the presence of TBAF in THF.

18
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- We have recently reported that allylsilanes are versatile synthetic intermediates in the presence of Lewis acid as an activator. In this case, however the Lewis acid works as an activator of carbonyl compounds or acetals rather than allylsilanes.
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- in press
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21
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- All products gave satisfactory spectral data and correct, elemental analysis.

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