Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

Literature DB >> 23663099

Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

Ryan J Felix¹, Osvaldo Gutierrez, Dean J Tantillo, Michel R Gagné.

Abstract

Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.

Entities: CellLine Chemical Disease Gene

Mesh：

Substances：

Year: 2013 PMID： 23663099 PMCID： PMC3788353 DOI： 10.1021/jo400139g

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

25 in total

1. Enzyme Mechanisms for Polycyclic Triterpene Formation.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-08-18 Impact factor: 15.336

2. Lessons and revelations from biomimetic syntheses.

Authors: Mina Razzak; Jef K De Brabander
Journal: Nat Chem Biol Date: 2011-11-15 Impact factor: 15.040

3. Synthesis of Unusually Strained Spiro Ring Systems and Their Exploits in Synthesis.

Authors: Richard J Duffy; Kay A Morris; Daniel Romo
Journal: Tetrahedron Date: 2009-09-01 Impact factor: 2.457

Review 4. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors: Ryan A Yoder; Jeffrey N Johnston
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

5. Strain energy release and intrinsic barriers in internal nucleophilic reactions.

Authors: Joel L Wolk; Esther Rozental; Harold Basch; Shmaryahu Hoz
Journal: J Org Chem Date: 2006-05-12 Impact factor: 4.354

6. Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors: Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal: Chem Rev Date: 2007-07 Impact factor: 60.622

7. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors:
Journal: Phys Rev B Condens Matter Date: 1988-01-15

8. Phosphine gold(I) bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes.

Authors: Nicolas Mézailles; Louis Ricard; Fabien Gagosz
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

1. Enzyme Mechanisms for Polycyclic Triterpene Formation.

2. Lessons and revelations from biomimetic syntheses.

3. Synthesis of Unusually Strained Spiro Ring Systems and Their Exploits in Synthesis.

Review 4. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

5. Strain energy release and intrinsic barriers in internal nucleophilic reactions.

6. Transition metal chemistry of cyclopropenes and cyclopropanes.

7. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

8. Phosphine gold(I) bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes.

9. Cyclobutanes in catalysis.

10. Eight-membered ring construction by [4 + 2 + 2] annulation involving beta-carbon elimination.

1. Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes.

2. Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.

3. Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes.

4. Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes.