Exploiting Non-Covalent Interactions in Synthesis: Macrocyclization Employing Amide-Based Auxiliaries

Autor:	Andreea R. Schmitzer, Shawn K. Collins, Lisa Bouillerand, Joseph E. Zakarian, Yassir El-Azizi
Rok vydání:	2008
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Olefin fiber Olefin metathesis Chemistry Stereochemistry Amide Non-covalent interactions General Chemistry Metathesis Conformational isomerism
Zdroj:	Advanced Synthesis & Catalysis. 350:2219-2225
ISSN:	1615-4169 1615-4150
DOI:	10.1002/adsc.200800365
Popis:	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.
Databáze:	OpenAIRE
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