2005
DOI: 10.1021/ol0506821
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Efficient Protiodesilylation of Unactivated C(sp3)−SiMe2Ph Bonds Using Tetrabutylammonium Fluoride

Abstract: [reaction: see text] The protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds proceeds efficiently by treatment with tetrabutylammonium fluoride in wet DMF or THF via isolable dimethylsilanol intermediates.

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Cited by 48 publications
(38 citation statements)
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“…Heating 17 with TBAF in a microwave oven furnished the unsaturated lactam 18 . 9 Epoxidation of 18 with peroxytrifluoroacetic acid in the presence of sodium carbonate gave a single epoxide 19 . 10 Although the epoxidation could be performed in unbuffered media, the ketal moiety was cleaved.…”
mentioning
confidence: 99%
“…Heating 17 with TBAF in a microwave oven furnished the unsaturated lactam 18 . 9 Epoxidation of 18 with peroxytrifluoroacetic acid in the presence of sodium carbonate gave a single epoxide 19 . 10 Although the epoxidation could be performed in unbuffered media, the ketal moiety was cleaved.…”
mentioning
confidence: 99%
“…The competing protodesilylation reaction with TBAF is minimized by maintaining the reaction at 0 8C and controlling the reaction time. [19] In summary, we have demonstrated the first example of an asymmetric catalytic [3+2] annulation reaction of allylsilanes and an efficient enantioselective synthesis for 3'-silyl-and 3'- [a] All reactions performed under argon with ScCl 3 (THF) 3 , NaSbF 6 , and 3 equiv of the allylsilane 2 a with ligand L. Thermal ellipsoids of the X-ray structure of 3 h are shown at 50 % probability.…”
mentioning
confidence: 96%
“…9 We initially targeted aldehydes 11 for use in chelate-controlled [3+2]-annulation reactions with 6 , since this would introduce the correct number of carbon atoms in the C(3) substituent of tetrahydrofuran 12 . The dithiane unit in 12a and the benzyl ether in 12b would also be sufficiently robust to survive the Hudrlik conditions10 that we initially contemplated using for protiodesilylation of 12 (a milder protocol for protiodesilylation was subsequently developed) 11. However, all attempts to effect the chelate-controlled [3+2]-annulation reactions of 6 with either 11a or 11b and a variety of chelating Lewis acids (SnCl 4 , TiCl 4 , etc) failed to provide more than trace amounts of the 2,5- trans -tetrahydrofurans 12 ; rather, the 2,5- cis -tetrahydrofuran isomer (not shown) was obtained preferentially, indicating that the dithiane and benzyl ether units of 11a,b were incapable of forming a kinetically competent concentration of β-chelate with the aldehyde 12…”
mentioning
confidence: 99%