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 Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Literature DB >> 17455944

Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Gilles Lemière¹, Vincent Gandon, Kevin Cariou, Takahide Fukuyama, Anne-Lise Dhimane, Louis Fensterbank, Max Malacria.

Abstract

We have developed an expedient method for the synthesis of polycyclic compounds from propargyl acetates or vinyl allenes involving up to three Au(I)-catalyzed elemental steps: 3,3-rearrangement, metalla-Nazarov reaction, and electrophilic cyclopropanation. The reaction proceeds under very mild conditions and in short times. The mechanism has been studied by DFT computations.

Entities: Chemical

Year: 2007 PMID： 17455944 DOI： 10.1021/ol070788r

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

Keyword Cloud
Cited

21 in total

1. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Authors: Paul Ha-Yeon Cheong; Philip Morganelli; Michael R Luzung; K N Houk; F Dean Toste
Journal: J Am Chem Soc Date: 2008-03-08 Impact factor: 15.419

2. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors: Nathan D Shapiro; F Dean Toste
Journal: Synlett Date: 2010-03-01 Impact factor: 2.454

3. Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors: Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2010-12-29 Impact factor: 15.336

Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

1. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

2. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

3. Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

4. Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Review 5. Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

6. Gold-catalyzed transannular [4+3] cycloaddition reactions.

7. Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

8. Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

9. Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

10. Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.