Formation of quaternary centres by copper catalysed asymmetric conjugate addition to [small beta]-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship

Formation of quaternary centres by copper catalysed asymmetric conjugate addition to [small beta]-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship. Ardkhean, R., Mortimore, M., Paton, R. S, & Fletcher, S. P Chemical Science, 9(9):2628–2632, 2018. Publisher: The Royal Society of Chemistry

Paper doi abstract bibtex

A new asymmetric conjugate addition method was developed for [small beta]-substituted cyclopentenones to form quaternary centres using alkylzirconocene nucleophiles giving up to 97% yield and 92% ee. Key to the reaction's success was the design of suitable phosphoramidite ligands which was aided by a linear quantitative structure-selectivity relationship (QSSR). QSSR models were created from the ligand screening data (a total of 36 ligands) which revealed important electronic and steric requirements and led to the synthesis of more enantioselective ligands. DFT calculations of competing transition structures enable the interpretation of the electronic and steric terms present in the QSSR models.

@article{ardkhean_formation_2018,
	title = {Formation of quaternary centres by copper catalysed asymmetric conjugate addition to [small beta]-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship},
	volume = {9},
	issn = {2041-6520},
	url = {http://dx.doi.org/10.1039/C7SC05304E},
	doi = {10.1039/C7SC05304E},
	abstract = {A new asymmetric conjugate addition method was developed for [small beta]-substituted cyclopentenones to form quaternary centres using alkylzirconocene nucleophiles giving up to 97\% yield and 92\% ee. Key to the reaction's success was the design of suitable phosphoramidite ligands which was aided by a linear quantitative structure-selectivity relationship (QSSR). QSSR models were created from the ligand screening data (a total of 36 ligands) which revealed important electronic and steric requirements and led to the synthesis of more enantioselective ligands. DFT calculations of competing transition structures enable the interpretation of the electronic and steric terms present in the QSSR models.},
	number = {9},
	journal = {Chemical Science},
	author = {Ardkhean, Ruchuta and Mortimore, Mike and Paton, Robert S and Fletcher, Stephen P},
	year = {2018},
	note = {Publisher: The Royal Society of Chemistry},
	pages = {2628--2632},
}

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