1161882-83-2Relevant academic research and scientific papers
Exploiting non-covalent interactions in synthesis: Macrocyclization employing amide-based auxiliaries
El-Azizi, Yassir,Zakarian, Joseph E.,Bouillerand, Lisa,Schmitzer, Andreea R.,Collins, Shawn K.
supporting information; experimental part, p. 2219 - 2225 (2009/10/08)
Efficient macrocyclic olefin and en-yne metathesis can be conducted employing benzyl ester auxiliaries that engage in quadrupolar interactions. The use of amide linkers in place of esters results in higher overall yields. Computational studies suggest that amide auxiliaries stabilize conformers conducive to macrocyclization over 22 times more efficiently than an ester linkage. Molecular modelling studies also suggest a preference for engaging in quadrupolar interaction for the amide auxiliaries, in contrast to the lone-pair (lp):π interactions predicted for ester-based auxiliaries.
