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

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...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/C7SC05304E

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
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Name:
Engineering and Physical Sciences Research Council
Grant:
CentreforDoctoralTraininginSynthesisforBiology
Medicine(EP/L015838/1
Publisher:
Royal Society of Chemistry
Journal:
Chemical Science More from this journal
Volume:
9
Issue:
9
Pages:
2628-2632
Publication date:
2018-02-05
Acceptance date:
2018-02-02
DOI:
ISSN:
2041-6520
Pubs id:
pubs:822895
UUID:
uuid:1d1f2113-5441-4b3e-8c7b-ecb587664fc7
Local pid:
pubs:822895
Source identifiers:
822895
Deposit date:
2018-02-05

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