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1. The additions of bromine to (E)- and (Z)-3-hexene are stereospecific! Give the structures of the products and explain the results!

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Stereochemistry Name:

Hans Reißig

Problem Set No. 5 (21.5.2013)

1. The additions of bromine to (E)- and (Z)-3-hexene are stereospecific! Give the structures of the products and explain the results!

2. Suggest two alternative methods to enantioselectively prepare (R)-1-phenylpropan-1-ol!

3. a) The reaction of D-proline with phosgene in the presence of NEt

3

provides a bicyclic compound which can be transformed into the R-configured CBS catalyst in one step (give all steps and reagents)!

1

(2)

2

b) Do a reduction of α-chloroacetophenone with this catalyst! Which face of this ketone will be attacked in preference, Re or Si?

c) By treatment with base the resulting product will form an epoxide! Write down this reaction and give the configuration of the resulting product!

4. Reduce methyl 4-oxopentanoate with baker´s yeast and treat the resulting product with acid to provide a γ-lactone!

5. The diastereoselective addition of cyanide using cyano(trimethyl)silane (in the presence of a catalytic amount of Lewis base) to (R)-2-benzyloxypropanal follows the Felkin-Anh rule.

Draw the major product and assign the absolute configuration of the two stereogenic centers!

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