i need to know the mechanism for the sorenson reaction?

Question

i need to know the mechanism for the sorenson method of amino acid synthesis. please help me find a link, or if you know a textbook that explains it

.. and if posible, a mech for the malonic ester amino acid synthesis

Answer 1

Sorensen method and the malonic ester amino acid synthesis are similar. Both involve an active methylene group (methylene group flanked by 2 EWGs). In the Sorensen method, you take N-acetylaminomalonic ester (EtOOC)2 CHNHCOCH3. Hydrolysis and decorboxylation of the product gives an alpha amino acid.

In the malonic ester amino acid synthesis, malonic ester is treated with the base followed by bromine to get alpha bromo derivative. The alpha bromo derivative is treated with ammonia to get alpha amino derivative. Amino group of this derivative is protected by acetic anyhdride. Base is added to get the carbanion once again and alkylated. Hydrolysis of this gives desired alpha amino acid.

Answer 2

my favorite for named reactions is:
http://www.monomerchem.com/display4.html

but i just got a great book written by grad students for grad students:
Strategic applications of named reactions in organic synthesis.

this has a lot of stuff in it and it's been very helpful for me

Answer 3

you can try this webby:


www.organic.chemistry.org

it helps~