key term - Methyl 2-oxocyclohexanecarboxylate

Definition

Methyl 2-oxocyclohexanecarboxylate is a cyclic ester compound that contains a cyclohexane ring with a carbonyl group and a methyl ester group. It is a key intermediate in the Dieckmann cyclization, a type of intramolecular Claisen condensation reaction.

5 Must Know Facts For Your Next Test

1. Methyl 2-oxocyclohexanecarboxylate is a key intermediate in the Dieckmann cyclization, a powerful method for forming cyclic ketones.
2. The cyclohexane ring in methyl 2-oxocyclohexanecarboxylate provides conformational rigidity and influences the stereochemistry of the final product.
3. The methyl ester group is important for the intramolecular attack of the enolate ion during the Dieckmann cyclization.
4. Methyl 2-oxocyclohexanecarboxylate can be synthesized from the corresponding diester precursor through a base-catalyzed intramolecular Claisen condensation.
5. The Dieckmann cyclization using methyl 2-oxocyclohexanecarboxylate is a widely used strategy in the synthesis of various cyclic ketones and natural products.

Review Questions

• Explain the role of methyl 2-oxocyclohexanecarboxylate in the Dieckmann cyclization reaction.
  • Methyl 2-oxocyclohexanecarboxylate is a key intermediate in the Dieckmann cyclization, which is a type of intramolecular Claisen condensation reaction. In this reaction, the ester group of the methyl 2-oxocyclohexanecarboxylate undergoes nucleophilic attack by an enolate ion formed from the other ester group, leading to the formation of a cyclic β-keto ester product. The cyclohexane ring in the methyl 2-oxocyclohexanecarboxylate provides conformational rigidity and influences the stereochemistry of the final cyclic ketone product.
• Describe the structural features of methyl 2-oxocyclohexanecarboxylate that make it a suitable precursor for the Dieckmann cyclization.
  • Methyl 2-oxocyclohexanecarboxylate possesses several structural features that make it a suitable precursor for the Dieckmann cyclization. The cyclohexane ring provides conformational rigidity and influences the stereochemistry of the final product. The methyl ester group is crucial for the intramolecular attack of the enolate ion during the cyclization step. Additionally, the carbonyl group in the 2-position of the cyclohexane ring is positioned to participate in the Claisen condensation reaction, leading to the formation of the cyclic β-keto ester product.
• Evaluate the synthetic utility of the Dieckmann cyclization using methyl 2-oxocyclohexanecarboxylate, and discuss its applications in the synthesis of natural products and other cyclic compounds.
  • The Dieckmann cyclization using methyl 2-oxocyclohexanecarboxylate is a powerful synthetic tool that has been widely employed in the synthesis of various cyclic ketones and natural products. The ability to form a cyclic β-keto ester from a simple diester precursor makes this reaction highly versatile and efficient. The conformational rigidity and stereochemical control provided by the cyclohexane ring in methyl 2-oxocyclohexanecarboxylate further enhances the synthetic utility of this intermediate. Numerous natural products and other complex cyclic compounds have been synthesized using the Dieckmann cyclization, demonstrating its broad applicability in organic synthesis.

Related terms

Dieckmann Cyclization:

A type of intramolecular Claisen condensation reaction that forms a cyclic ketone from a diester precursor.

Intramolecular Claisen Condensation:

A reaction where an enolate ion attacks an ester group within the same molecule, forming a cyclic β-keto ester.

Enolate Ion:

A negatively charged intermediate formed by the removal of a proton from the α-carbon of a carbonyl compound.