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Synthesis 2015; 47(15): 2256-2264
DOI: 10.1055/s-0034-1380702
DOI: 10.1055/s-0034-1380702
special topic
Cyclic Model for the Asymmetric Conjugate Addition of Organolithiums with Enoates
Weitere Informationen
Publikationsverlauf
Received: 14. März 2015
Accepted after revision: 13. April 2015
Publikationsdatum:
19. Mai 2015 (online)
Abstract
The chiral diether ligand controlled asymmetric conjugate addition of organolithiums to nona-2,7-dienedioates preferentially proceeds via the s-cis conformation with coordination of the carbonyl oxygen atom to the lithium to give a lithium E-enolate intermediate. Subsequent intramolecular conjugate addition of the enolate also proceeds via a cyclic transition state involving the lithium and the s-cis-enoate, resulting in trans,trans-trisubstituted cyclohexanes with high enantiomeric excesses and yields.
Key words
chiral ligand - asymmetric synthesis - organolithiums - conjugate addition - cascade reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380702.
- Supporting Information
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For C-nucleophiles, see:
For N-nucleophiles, see:
For S-nucleophiles, see ref. 2g and:
For diastereoselective conjugate addition cascades of dienedioates, see:
For our other approaches to conjugate addition triggered cascade reactions, see:
For our preliminary reports, see: