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Problem Set No. 6 1. Provide the following intermediates and product. What is the name of this reaction?

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Modern Synthetic Methods Name:

D. Tyler McQuade

Problem Set No. 6

1. Provide the following intermediates and product. What is the name of this reaction?

O O

Br

CuCl (1 mol%), Cs

2

CO

3

(2 eq.) pivalic acid (1.2 eq), DMF

130

o

C, 7h

CuCl

O O

Br

Oxidative addition Cs

2

CO

3

CsOPiv

CsBr Cu O

O

Cl O O Cs CsOPiv

Reductive Elimination Product

Product

2. Provide the reagents

(2)

3. Draw the products

4. Draw the product.

5. Read Hoveyda et al. Angew. Chem. Int. Ed. 2012, 51, 6618 –6621. How did the authors

use their method to synthesize a fragment of aza-epithialone A? How do the authors justify

their observed stereochemical induction?

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