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Literature DB >> 15932209

Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Cheryl L Heitzman¹, William T Lambert, Eric Mertz, J Brad Shotwell, Jennifer M Tinsley, Porino Va, William R Roush.

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.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15932209 PMCID： PMC2515625 DOI： 10.1021/ol0506821

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

8 in total

1. [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.

Authors: Zhi-Hui Peng; K A Woerpel
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

2. Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

Authors: G C Micalizio; W R Roush
Journal: Org Lett Date: 2001-06-14 Impact factor: 6.005

3. A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent.

Authors: G C Micalizio; W R Roush
Journal: Org Lett Date: 2000-02-24 Impact factor: 6.005

4. Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions.

Authors: James C Anderson; Rachel H Munday
Journal: J Org Chem Date: 2004-12-10 Impact factor: 4.354

5. An efficient [4 + 2 + 1] entry to seven-membered rings.

Authors: Yike Ni; John Montgomery
Journal: J Am Chem Soc Date: 2004-09-15 Impact factor: 15.419

6. Synthesis of the C11-C29 fragment of amphidinolide F.

Authors: J Brad Shotwell; William R Roush
Journal: Org Lett Date: 2004-10-14 Impact factor: 6.005

7. The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling.

Authors: James C Anderson; Stéphane Anguille; Rosalyn Bailey
Journal: Chem Commun (Camb) Date: 2002-09-21 Impact factor: 6.222

8. Synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation.

Authors: Zhi-Hui Peng; K A Woerpel
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

8 in total

14 in total

1. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors: Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

2. Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

Authors: Lei Chen; Zhengmao Hua; Gangqin Li; Zhendong Jin
Journal: Org Lett Date: 2011-06-14 Impact factor: 6.005

3. Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

Authors: Jie Wu; Yu Chen; James S Panek
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

1. [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.

2. Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

3. A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent.

4. Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions.

5. An efficient [4 + 2 + 1] entry to seven-membered rings.

6. Synthesis of the C11-C29 fragment of amphidinolide F.

7. The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling.

8. Synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation.

1. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

2. Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

3. Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

4. Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

5. Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

6. Siloxacyclopentenes as dienophile-linked directing groups in intramolecular Diels-Alder reactions.

7. Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

8. Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

9. Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.

10. Intermolecular silacarbonyl ylide cycloadditions: a direct pathway to oxasilacyclopentenes.