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Problem Set No. 4_Key 1. Fill in the missing structures and provide an arrow pushing mechanism for the reaction using the Schwartz reagent.

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Modern Synthetic Methods Name:

D. Tyler McQuade

Problem Set No. 4_Key

1. Fill in the missing structures and provide an arrow pushing mechanism for the reaction using the Schwartz reagent.

O O O

O

2. Provide a mechanism for the following reaction making sure to explain both products and observed stereochemistry.

3. Provide an example from the literature and a mechanism for the following reactions:

a. Corey-Chaykovsky Cyclopropanation

TMS

OEt

LDA, EtOAc, THF

-78oC, 1 h, EtO O TMS

Enzymatic

Reduction EtO

OH TMS

K2CO3aq.,

THF, MeOH HO

OH H

TIPSOTf, 2,6-lutidine, CH2Cl2,

-40oC to -20oC TIPSO

O O O

OTIPS H

i) Cp2ZrHCl, CH2Cl2

ii) I2,CH2Cl2,0oC, 7 h TIPSO

OTIPS I

K2CO3

THF, MeOH HO

OTIPS I

(2)

b. Furukawa-Simmons-Smith Cyclopropantion

4. What is the name of the following reaction? Draw the products formed and their stereochemical relationship. Draw the nucleophilic zinc species that is formed.

Reformatsky Reaction

Referenzen

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