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Chapter 9: Q81. (page 382)

Question: Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60掳 bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y

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01

Step-by-Step SolutionStep 1: Neighboring group participation

The reactive site interacts with the electrons in the lone pairs on the group attached to the side by carbon by either sigma or pi-bond.

The neighboring group participation leads to an increase in the rate of the reaction.

02

Intermediates

Intermediates are either short-lived or long-lived chemical species. These can be separated from the reaction.

03

Products of the given reactions

The conversion mechanism of X to form Y indicating the structure of aziridine intermediate and the trans stereochemistry of the two amines in Y is given hereunder:

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