5. The target compound below (a potential ẞ-blocker drug) may be prepared using a sulfonium ylide (and then a 2° amine) according to the retrosynthetic scheme shown below. Please perform the following: (a) Draw the structure of a suitable ylide that would accomplish this task and (b) write a mechanism to depict the formation and subsequent usage of the ylide (for the reaction in which the aldehyde is converted into the epoxide)...so the mechanism does NOT have to include the amine + epoxide part of the synthesis. HO NR₂ potential class of B-blocker drugs sulfonium ylide

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.67P
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5. The target compound below (a potential ẞ-blocker drug) may be prepared using a sulfonium ylide (and
then a 2° amine) according to the retrosynthetic scheme shown below. Please perform the following:
(a) Draw the structure of a suitable ylide that would accomplish this task and (b) write a mechanism to
depict the formation and subsequent usage of the ylide (for the reaction in which the aldehyde is
converted into the epoxide)...so the mechanism does NOT have to include the amine + epoxide part of
the synthesis.
HO
NR₂
potential class of
B-blocker drugs
sulfonium ylide
Transcribed Image Text:5. The target compound below (a potential ẞ-blocker drug) may be prepared using a sulfonium ylide (and then a 2° amine) according to the retrosynthetic scheme shown below. Please perform the following: (a) Draw the structure of a suitable ylide that would accomplish this task and (b) write a mechanism to depict the formation and subsequent usage of the ylide (for the reaction in which the aldehyde is converted into the epoxide)...so the mechanism does NOT have to include the amine + epoxide part of the synthesis. HO NR₂ potential class of B-blocker drugs sulfonium ylide
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