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2) Muller, P.; Siegfried, B. Helv. Chim. Acta. 1974, 57, 987-994.
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About Paper 1:
This paper helped to determine the mechanism of the first and last steps of our reaction, an esterification and the addition of an amide. The paper helped to describe how DMT-MM (Figure 1) enacted the reaction. This paper demonstrated that, when added to esters, DMT-MM allowed for carbonyl additions. Its positive charge allowed a deprotenated carboxylic acid to act as a nucleophile and attack the bond across from the positively charged nitrogen, placing a six-membered ring on the deprotenated carboxylic acid. Next the paper, through a diagram describing the mechanism (Figure 2), showed that the newly formed ester could be attacked by an alcohol, creating a precarious situation: The newly arriving alcohol would be available to protenate (or probably more accurately create a partial positive charge) a nitrogen of the ester, creating a positively charged, unfavorable nitrogen atom, and making the ester an excellent leaving group. The negatively charged oxygen could then kick down its electrons, allowing the formation of a carbonyl group on the DMT-MM, and an ester on "67".
Papers that cited paper 1:
1) Morieux, P.; Stables, J.P.; Kohn, H. Bioorgan. Med. Chem. 2008, 16, 8968-8975.
-This paper utilizes DMT-MM in the synthesis of an amide from carboxylic acids, citing the paper for proof of the functionality of this group for such a synthesis.
-After purifying the compounds created from the synthesis of the amides, enantiopurity was expected from the original paper.
-As is presented in our paper, this paper utilizes DMT-MM to allow for the attack on an ester by the desired product group.
2) Farkas, P.; Bystricky, S. Carbohyd. Polym. 2007, 68, 187-190.
-This paper cites the original paper as support to its focus, utilizing DMT-MM on polysaccharides to activate carboxylic acids.
-The paper also cites the original for its use of DMTMM in reactions with Sn2 reactions.
-The paper cites the original paper as support for its use of DMT-MM in a water solution also allowing for more certain structural purtity.
3) Moroy, G.; Denhex, C.; Mourabit, H.E.; Toribio, A.; Dassonville, A.; Decarme, M.; Renault, J.H.; Mirand, C.; Bellon, G.; Sapi, J.; Alix, A.J.; Hornebeck, W.; Bourguet, E. Bioorgan. Med. Chem. 2007, 15, 4753-4766.
-This paper cited the original for evidence as to the manner by which they produced succinyltryptophanamides from monoallyl esters.
-This paper uses the DMT-MM to choise the stereochemistry of the reaction, as it was used in the original paper.
-This paper uses DMT-MM as a coupling agent to convert esters directly into acids.