Formal Alkyne Insertion into Alkoxycarbene Complexes: Simple Access to Enantiopure Group 6 Alkynyl(alkoxy)carbene Complexes

Barluenga, José; Rúa, Ramón Bernardo de la; Saá, Diana de; Ballesteros, Alfredo; Tomás, Miguel

doi:10.1002/anie.200501400

Cited by 51 publications

(26 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Reaction of Fischer carbenes with alkoxyacetylides afforde new alkyne substituted carbenes (Eq. (396)) [1586]. …”

Section: Reactions Of Isolated Transitionmetal Complexes and Copper-mentioning

confidence: 97%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…Reaction of Fischer carbenes with alkoxyacetylides afforde new alkyne substituted carbenes (Eq. (396)) [1586]. …”

Section: Reactions Of Isolated Transitionmetal Complexes and Copper-mentioning

confidence: 97%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…5 At this point, it is worth to mention a report of [4+2] cycloaddition with the participation of chiral alkoxy(alkynyl) carbene complexes. In this work, Barluenga et al reported the only example to date of synthesis of enantiopure alkoxy(alkynyl)carbene complexes, compounds that are not accessible following conventional procedures [35]. Moreover, it is described the participation of carbene 51 in the synthesis of enantiopure 1,4-dihydropyridinecarbene 53 through an asymmetric [4+2] cycloaddition.…”

Section: Scheme 17mentioning

confidence: 94%

Fischer-Type Group 6 Carbene Complexes in the Synthesis of Optically Active Molecules

Santamarı́a

2009

COC

View full text Add to dashboard Cite

In the last decades Group 6 Fischer Carbene complexes have demonstrated their ability as an interesting tool in asymmetric synthesis. The use of this family of organometallic compounds permitted the access to a wide array of optically active and occasionally enantiopure molecules. In this sense, carbo-and heterocycles of different sizes -from three to eighth membered rings-along with open chain compound, have been synthesized. Additionally, the use of Fischer carbene complexes has, in some cases, dramatically simplified the access to some natural or biologically active molecules only accessible following other tedious methodologies. The synthesis of optically active molecules from Group 6 Fischer carbene complexes will be reviewed here from two points of view: from chiral and from achiral carbene complexes. Among the enantiopure carbene complexes a distinction between amino an alkoxycarbenes has been formulated. On the other hand, asymmetric synthesis with chiral alkoxycarbenes has been divided in three groups according to the position of the inductor of chirality: i) in the stabilizing group, ii) in the carbene ligand, iii) in the coordination sphere ligands. Finally, all the sections along this review have been subdivided according to the reaction type.

show abstract

“…Barluenga and co-workers report an enantioselective synthesis of 1,4-dihydropyridine 56 by reaction of the chiral alkynyl-(alkoxy)carbene complex 54 with 1-azadiene 53 (Scheme 15). 52 The dihydropyridine complex 55 was isolated in 70% yield as a single regio-and diastereoisomer. The complex was demetallated and the chiral auxiliary removed by treatment with [Cu-(MeCN) 4 ]BF 4 in wet dichloromethane, giving the corresponding optically pure (ee 4 99.5%) aldehyde 56 in 65% yield.…”

Section: [4 + 2] Cycloadditions/hetero-diels-alder Reactionsmentioning

confidence: 99%

1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles

2008

View full text Add to dashboard Cite

1-Azadienes are versatile building blocks for the efficient construction of various N-heterocycles. Depending on the substitution pattern and reaction partner, they may participate in a range of different reactions. An overview of recent methods for the generation of 1-azadienes is presented, as well as their application in cycloaddition, electrocyclization, and multicomponent reactions. Considering the broad range of reactivities and resulting heterocyclic scaffold structures, 1-azadienes are very useful reactive intermediates for the development of modular reaction sequences in diversity-oriented synthesis.

show abstract

Formal Alkyne Insertion into Alkoxycarbene Complexes: Simple Access to Enantiopure Group 6 Alkynyl(alkoxy)carbene Complexes

Cited by 51 publications

References 36 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Fischer-Type Group 6 Carbene Complexes in the Synthesis of Optically Active Molecules

1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles

Contact Info

Product

Resources

About