Homepage Mechanism Experimental NMR Correlations Leading Question About Us
References: Welcome to the Bay of Islands

Davies, H. M. L.; Grazini, M. V. A.; Aouad, E.; Org. Lett. 2001, 3, 1475-1477.

Screen Shot 2015-04-02 at 9.06.33 AM.png

This paper investigates the stereo- and regio-selectivity of intramolecular rhodium-catalysed C-H insertion reactions.

Fu, L.; Wang, H.; Davies, H. M. L. Org. Lett. 2014, 16, 3036-3039.

Paper_1.PNG

The reaction shown above is an intramolecular ring closure catalyzed by rhodium.  This specific pair of rhodium catalyst and solvent produce the best yield of the desired cis stereoisomer.  Similar to our reaction, these authors use dichloromethane as a solvent.  They also use a similar rhodium catalyst; theirs is just a bit more bulky than rhodium acetate.  This leads to an even higher amount of stereoselectivity than was reported in our paper.

Wang, H.; Li, G.; Engle, K. M.; Yu, J.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6774-6777.

Paper_2.PNG

The above reaction is the intermolecular formation of a five-membered ring (again catalyzed by rhodium).  It is also very similar to the reaction in our main paper, except that this reaction is intermolecular, whereas ours is intramolecular.  This one also has a major product of the trans diastereomer, which is not the one in our reaction.  The authors achieve high stereoselectivity with a rhodium catalyst.

Ito, M.; Namie, R.; Krishnamurthi, J.; Miyamae, H.; Takeda, K.; Nambu, H.; Hashimoto, S. Synlett 2014, 25, 288-292.

Screen Shot 2015-03-18 at 12.26.44 PM.png

The reaction shown above is a cis-diastereoselective intramolecular ring closure.  this is very similar to out reaction, the only differences being additional substitution on the phenyl ring and the presence of a chiral auxiliary.  These authors, however, use toluene, a relatively nonpolar solvent, in place of dichloromethane.