REFERENCES:

Original Article Containing our Reaction:

O'Malley, D.P.; Li, K.; Maue, M.; Zografos, A.L.; Baran, P.S. J. Am. Chem. Soc. 2007, 129 (15), 4762-4775.

 

Citations in our Paper:

Reference 39a)

Heinrich, N.; Koch, W.; Frenking, G.; Schwarz, H. J. Am. Chem. Soc. 1986, 108, 593-600.

Reference 39b)

Rosenberg, R. E. J. Org. Chem. 1998, 63, 5562-5567.

Reference 41 (covering the reactions of (+)-79 to (+)-34 and (-)-73 to (-)-34):

Chern, C.Y.; Huang, Y.-P.; Kan, W.M. Tetrahedron Lett. 2003, 44, 1039-1041.

 

Contents of Reference 41:

In the reaction, the amine that is undergoing methanolysis is protected by a benzyl group. Article five cites another article that details a method for debenzylating benzyl-protected amides. Normally, this reaction requires very harsh conditions to remove the highly electrophilic benzyl cations. This article proposes a milder reaction scheme to remove the benzyl group. In our reaction, for the methanolysis to occur, the benzyl group must be removed. In our particular reaction, the conditions listed in the article (TsOH) are used. The reaction can run under even milder conditions due to the transition state formed by the nucleophilic addition of the nitrogen to the adjacent carbonyl. These milder conditions allow for a removal of the benzyl protecting group without damaging other functional groups.

 

 

Papers Referencing 41:

First Work Citing the Journal

Pinna, N.; Garnweitner, G.; Antonietti, M.; Niederberger, M. J. Am. Chem. Soc. 2005, 127, 5608-5612.

This article details an alternative method of deprotecting amides. Instead of TsOH, this reaction scheme uses an organometallic complex of an enolate with iron. This work cited the first article's reaction because they were using our citation as a theoretical comparison.

 

Second Work Citing this Journal

Paik, S.; Lee, J. Y. Tetrahedron Lett. 2006, 47, 1813-1815.

This article discusses how different groups substituted onto the methylene group of the benzyl protecting group affect the deprotection reaction. It cited the first article's reaction as conditions for a deprotection and to get an idea for how quickly certain basic substituents would react.

 

Third Work Citing this Journal

Trost, B. M.; Fandrick, D. R. Org. Lett. 2005, 7, 823-826.

This article cited the first article's reaction scheme as a mild way of deprotecting an amine. It then used the mild deprotection mechanism to change the substituents on their nitrogens witout affecting the double bond.