Functional Group Transformations Oxidation and reduction

Discovery consists of seeing what everybody has seen and thinking what nobody 

Chapter 4 centers on two key transformations in organic synthesis (1) oxidation of alcohols and of unsaturated hydrocarbons (i.e., alkenes and alkynes) to carbonyl compounds (2) reduction of various carbonyl compounds to alcohols. 

Problem 1 emphasizes reagents for oxidation and reduction. Problems 2-4, stress the selectivity of oxidations and reductions in reaction sequences. Syntheses of Problem 5 TMs require choosing specific reagents to achieve chemo-, stereo-, or enantioselective oxidations or reductions. 

Reagents. Give the structure of the major products (A-H) expected from the following reactions. Be sure to indicate product stereochemistries. Assume that standard aqueous workup conditions are used for product isolation. 

Steo 1 Dess-Martin periodinane oxidation. Step 2 Reductive amination. 

Step 2a Utilization of 1 eq of diisobutylaluminum hydride (DIBAL-H) ensures reduction of the ester group stops to the corresponding aldehyde. 

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Chapter 4 Functional Group Transformations Oxidation and Reduction... 

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