Question 1 Compound A below undergoes Dieckmann cyclization to give compound B, in the presence of a base. Dieckmann 3-step synthesis ÇH3 cyclisation CHCH OEt Eto OEt CH3 Ô Base H3C CH3 H3C CH3 A B.
Question 1 Compound A below undergoes Dieckmann cyclization to give compound B, in the presence of a base. Dieckmann 3-step synthesis ÇH3 cyclisation CHCH OEt Eto OEt CH3 Ô Base H3C CH3 H3C CH3 A B.
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 17MP
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a) Give the appropriate base for the above reaction and draw the resonance structures of the enolate ions derived from compound A. Then write the mechanism for the formation of the Dieckmann cyclized product B.
b) If compound B above is reacted with NaBH 4 , draw the structure of the reduced product. Give a reason for your choice of product.
c) Being a β-ketoester, B could undergo a 3-step synthesis involving alkylation, hydrolysis and decarboxylation reactions to yield the cyclopentanone, C. Write the outline synthesis for each step which include the appropriate regents and correct intermediate.
Transcribed Image Text:Question 1
Compound A below undergoes Dieckmann cyclization to give compound B, in the presence of a base.
CH3
Dieckmann
3-step
OEt
cyclisation
synthesis
CHCH3
Eto
OEt
CH3 Ô
Base
H3C
CH3
H3C
CH3
A
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