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Literature DB >> 27626462

A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Stephen D Holmbo¹, Nicole A Godfrey¹, Joshua J Hirner¹, Sergey V Pronin¹.

Abstract

A catalytic formal ene reaction between ketone-derived silyl enol ethers and terminal alkynes is described. This transformation is uniquely capable of bimolecular assembly of 2-siloxy-1,4-dienes and can be used to access β,γ-unsaturated ketones containing quaternary carbons in the α-position.

Entities: Chemical Disease Gene

Year: 2016 PMID： 27626462 PMCID： PMC6791363 DOI： 10.1021/jacs.6b06847

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

52 in total

1. Catalytic asymmetric vinylation of ketone enolates.

Authors: A Chieffi; K Kamikawa; J Ahman; J M Fox; S L Buchwald
Journal: Org Lett Date: 2001-06-14 Impact factor: 6.005

2. Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates. Synthesis Of bridged azabicyclic compounds

Authors:
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

3. A highly convergent cascade cyclization to cis-hydrindanes with all-carbon quaternary centers and its application in the synthesis of the aglycon of dendronobiloside A.

Authors: Yejian Han; Lizhi Zhu; Yuan Gao; Chi-Sing Lee
Journal: Org Lett Date: 2011-01-10 Impact factor: 6.005

4. Gold(I)-catalyzed cyclizations of silyl enol ethers: application to the synthesis of (+)-lycopladine A.

Authors: Steven T Staben; Joshua J Kennedy-Smith; David Huang; Britton K Corkey; Rebecca L Lalonde; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2006-09-11 Impact factor: 15.336

5. Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

Authors: Francis Barabé; Patrick Levesque; Ilia Korobkov; Louis Barriault
Journal: Org Lett Date: 2011-09-15 Impact factor: 6.005

6. Total synthesis of the Daphniphyllum alkaloid daphenylline.

Authors: Zhaoyong Lu; Yong Li; Jun Deng; Ang Li
Journal: Nat Chem Date: 2013-06-30 Impact factor: 24.427

7. Construction of methylenecycloheptane frameworks through 7-exo-dig cyclization of acetylenic silyl enol ethers catalyzed by triethynylphosphine-gold complex.

Authors: Hideto Ito; Hirohisa Ohmiya; Masaya Sawamura
Journal: Org Lett Date: 2010-10-01 Impact factor: 6.005

8. Regio- and stereoselective generation of alkenylindium compounds from indium tribromide, alkynes, and ketene silyl acetals.

Authors: Yoshihiro Nishimoto; Ryosuke Moritoh; Makoto Yasuda; Akio Baba
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

1. Catalytic asymmetric vinylation of ketone enolates.

2. Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates. Synthesis Of bridged azabicyclic compounds

3. A highly convergent cascade cyclization to cis-hydrindanes with all-carbon quaternary centers and its application in the synthesis of the aglycon of dendronobiloside A.

4. Gold(I)-catalyzed cyclizations of silyl enol ethers: application to the synthesis of (+)-lycopladine A.

5. Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

6. Total synthesis of the Daphniphyllum alkaloid daphenylline.

7. Construction of methylenecycloheptane frameworks through 7-exo-dig cyclization of acetylenic silyl enol ethers catalyzed by triethynylphosphine-gold complex.

8. Regio- and stereoselective generation of alkenylindium compounds from indium tribromide, alkynes, and ketene silyl acetals.

9. A Concise Approach to Paxilline Indole Diterpenes.

10. Palladium-catalyzed alkenylation of ketone enolates under mild conditions.

1. Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

2. Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.

3. Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones.

Review 4. Total synthesis of complex terpenoids employing radical cascade processes.

Review 5. Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies.