Atorvastatin (Lipitor) is a popular treatment for high cholesterol. See "The Importance ofHydrogen Bonding in Drug-Receptor Interactions"One synthesis of atorvastatin involves the following enolate reaction.Draw the predominant product of this reaction, which gives an overall yield of 90%.Но1. 2 Equiv. LDA, MgBr, -78°CNH3. H,OThere are a couple of noteworthy aspects to this reaction. First, MgBr, is added to ex-change with Li and make Mg enolates. This is helpful for controlling stereochemistry.Notice that the starting material is chiral and that a single enantiomer is used. The prod-uct of this reaction is a 97:3 (94% ee) mixture of two enantiomers, not a racemic mix-ture. You don't have to be able to deduce which enantiomer is the predominant product,but be aware that being able to control the stereochemical outcome of a reaction by us-ing a single enantiomer of a chiral starting material can save time and resources in thelarge-scale synthesis of chiral drugs.

The enolate ion formed in the reaction attacks the electrophilic carbon of the aldehyde group of the…

Answered: Atorvastatin (Lipitor) is a popular…

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 19.80P

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