Asked Dec 31, 2019

Besides asymmetric hydrogenation (Section 29.4), several other methods are now available for the synthesis of optically active amino acids. How might a reaction like the Strecker synthesis be adapted to the preparation of chiral amino acids?


Expert Answer

Step 1

The Strecker synthesis adapted for the preparation of chiral amino acids :


Chemistry homework question answer, step 1, image 1
Step 2

The mechanism can be given in two steps as :

Step 1: the carbonyl oxygen of an aldehyde is protonated, followed by a nucleophilic attack of ammonia to the carbonyl carbon. After subsequent proton exchange, water is cleaved from the iminium ion intermediate. A cyanide ion then attacks the iminium carbon yielding an aminonitrile.

Chemistry homework question answer, step 2, image 1
Step 3

Step 2: the nitrile nitrogen of the aminonitrile is protonated, and the nitrile carbon is attacked by a water molecule. A 1,2-diamino-diol is then formed after proton exchange and a nucleophilic attack ...

Chemistry homework question answer, step 3, image 1

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