Chromium and tungsten pentacarbonyl groups as reactivity auxiliaries in the Diels-Alder reactions of alkenyl carbene complexes with 1,3-dienes

Wulff, William D.; Bauta, William E.; Kaesler, Ralph W.; Lankford, Peter J.; Miller, Ross A.; Murray, Christopher K.; Yang, Dominic C.

doi:10.1021/ja00165a060

Cited by 171 publications

(47 citation statements)

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“…C, H and N elemental analyses were performed on a Perkin-Elmer 240 microanalyzer. Compounds 1a [15], 1b-d [16], 2 [10b], were prepared according to literature methods. Complex 3a has been described before [1b].…”

Section: General Methodsmentioning

confidence: 99%

Palladium(II) allylic complexes by carbene transmetalation and migratory insertion reactions: Synthesis and side reactions

Albéniz

Espinet

Pérez-Mateo

2010

Journal of Organometallic Chemistry

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Section: General Methodsmentioning

confidence: 99%

Palladium(II) allylic complexes by carbene transmetalation and migratory insertion reactions: Synthesis and side reactions

Albéniz

Espinet

Pérez-Mateo

2010

Journal of Organometallic Chemistry

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“…The other silyl enol ethers 5 were prepared in a similar way to the literature procedures. [26] (Alkenyl)(methoxy)carbene complexes 1, 2, [27] and 11 [28] were prepared according to literature procedures. Ketones 4 g and 4 l were prepared by addition of the corresponding organocuprate to acetyl bromide.…”

Section: Methodsmentioning

confidence: 99%

Diastereoselective Synthesis of Five‐ and Seven‐Membered Rings by [2+2+1], [3+2], [3+2+2], and [4+3] Carbocyclization Reactions of β‐Substituted (Alkenyl)(methoxy)carbene Complexes with Methyl Ketone Lithium Enolates

Barluenga

Alonso

Fañanás

2005

Chemistry A European J

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beta-Substituted alkenylcarbene complexes react with methyl ketone lithium enolates to give different carbocyclization products depending on the structure of the lithium enolate, on the metal of the carbene complex, and on the reaction media. Thus, the reactions of aryl and alkyl methyl ketone lithium enolates with beta-substituted alkenyl chromium and tungsten carbene complexes in diethyl ether afford 1,3-cyclopentanediol derivatives derived from a formal [2+2+1] carbocyclization reaction. However, the lithium enolates of acetone and tungsten complexes furnish formal [3+2+2] carbocyclization products. In the case of alkynyl methyl ketone lithium enolates, competitive formal [2+2+1] and [3+2] carbocyclization reactions occur and 1,3-cyclopentanediol and 3-cyclopentenol derivatives are formed. Conversely, alkenyl methyl ketone lithium enolates react with alkenylcarbene complexes under the same reaction conditions to form 2-cycloheptenone derivatives by a formal [4+3] carbocyclization reaction. Finally, when the reaction was performed in the presence of a coordinating medium, the [3+2] carbocyclization pattern was observed independently of the nature of the methyl ketone lithium enolate used.

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“…49 Aromatization can also occur during silica gel column chromatography (eq 25). 50 (21) Lewis Acidic Conditions. Five molar lithium perchlorate in ether is a suitable Lewis acid for promoting the [4 + 2] cycloaddition, and greatly enhances the reaction rate with a quinone as dienophile (eq 26): 51 aromatization also occured leading to a naphthaquinone derivative.…”

Section: R R'mentioning

confidence: 99%

1-Acetoxy-1,3-butadiene

Carpenter¹,

Coleman²,

Zhang³

et al. 2007

Encyclopedia of Reagents for Organic Synthesis

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AcO [1515-76-0] C 6 H 8 O 2 (MW 112.13) InChI = 1/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3 InChIKey = NMQQBXHZBNUXGJ-UHFFFAOYAQ (2π or 4π partner in cycloaddition reactions; 1 mono-oxygenation allows high levels of regiocontrol 2 ) Alternate Name: 1,3-butadienyl acetate. Physical Data: bp 60-61 • C/40 mmHg; d 0.945 g cm −3 . Form Supplied in: colorless liquid, available as an unspecified mixture of (E) and (Z) isomers. 3 Handling, Storage, and Precautions: classified as a flammable liquid and is reputed to be toxic. Compound polymerizes upon extended storage and can be regenerated by distillation. Avoid polymerization initiators. Diene performs best when stored in the cold.

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Chromium and tungsten pentacarbonyl groups as reactivity auxiliaries in the Diels-Alder reactions of alkenyl carbene complexes with 1,3-dienes

Cited by 171 publications

References 0 publications

Palladium(II) allylic complexes by carbene transmetalation and migratory insertion reactions: Synthesis and side reactions

Palladium(II) allylic complexes by carbene transmetalation and migratory insertion reactions: Synthesis and side reactions

Diastereoselective Synthesis of Five‐ and Seven‐Membered Rings by [2+2+1], [3+2], [3+2+2], and [4+3] Carbocyclization Reactions of β‐Substituted (Alkenyl)(methoxy)carbene Complexes with Methyl Ketone Lithium Enolates

1-Acetoxy-1,3-butadiene

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