Six-membered, chiral NHCs derived from camphor: structure-reactivity relationship in asymmetric oxindole synthesis
A series of three chiral, expanded six-membered NHC-palladium(II) complexes was prepared with successively increased sterical demand, while retaining natural d-(+)-camphor as a chiral motif. The catalysts showed different reaction profiles in the asymmetric, intramolecular α-arylation of amides. The...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
January 30, 2012
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| In: |
Organometallics
Year: 2012, Volume: 31, Issue: 3, Pages: 1127-1132 |
| ISSN: | 1520-6041 |
| DOI: | 10.1021/om201166b |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1021/om201166b Verlag, Volltext: https://doi.org/10.1021/om201166b 
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| Author Notes: | Markus J. Spallek, Dominic Riedel, Frank Rominger, A. Stephen K. Hashmi, and Oliver Trapp |
| Summary: | A series of three chiral, expanded six-membered NHC-palladium(II) complexes was prepared with successively increased sterical demand, while retaining natural d-(+)-camphor as a chiral motif. The catalysts showed different reaction profiles in the asymmetric, intramolecular α-arylation of amides. The molecular structure of two N-heterocyclic and one nitrogen acyclic carbene palladium isonitrile complex was unequivocally determined by X-ray crystallographic analysis. The results reported herein account for a correlation of catalytic activity and enantiodiscrimination in relation to the degree of chiral substitution and steric congestion at the metal center. The modular and convergent synthetic route of these air- and moisture-stable palladium isonitrile complexes underlines the usefulness of this approach. |
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| Item Description: | Gesehen am 03.08.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6041 |
| DOI: | 10.1021/om201166b |