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Issue 9, 2018
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Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure–selectivity relationship

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Abstract

A new asymmetric conjugate addition method was developed for β-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.

Graphical abstract: Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure–selectivity relationship

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Supplementary files

Article information


Submitted
14 Dec 2017
Accepted
02 Feb 2018
First published
05 Feb 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 2628-2632
Article type
Edge Article

Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure–selectivity relationship

R. Ardkhean, M. Mortimore, R. S. Paton and S. P. Fletcher, Chem. Sci., 2018, 9, 2628 DOI: 10.1039/C7SC05304E

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