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Chiral alkoxide-functionalized guanidinates from ring-opening rearrangement of aminooxazolinate complexes
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Gott, Andrew L., Coles, Stuart R., Clarke, Adam J., Clarkson, Guy J. and Scott, Peter (2007) Chiral alkoxide-functionalized guanidinates from ring-opening rearrangement of aminooxazolinate complexes. Organometallics, Vol.26 (No.1). pp. 136-142. doi:10.1021/om0607649 ISSN 0276-7333.
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Official URL: http://dx.doi.org/10.1021/om0607649
Abstract
Treatment of Cp*M(NMe2)(3) (M = Zr, Hf) with both achiral and optically pure chiral aminooxazoline proligands HL yields metastable aminooxazolinate half-sandwich diamide complexes [Cp*ML(NMe2)(2)]. These species undergo clean rearrangement via oxazoline ring-opening to carbodiimides followed by amide migratory insertion. The chiral-at-metal products contain tridentate alkoxide-functionalized guanidinates, as confirmed by X-ray diffraction. In some of the chiral ligand systems, single diastereomer samples can be prepared, either by direct reaction or after recrystallization. As a result of the chelate structure, no thermal conversion between diastereomers is observed. A mechanism leading to the observed diastereoselection involving an intramolecular CH-pi interaction in the major product is proposed.
| Item Type: | Journal Article | ||||
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| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Engineering > WMG (Formerly the Warwick Manufacturing Group) |
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| Journal or Publication Title: | Organometallics | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0276-7333 | ||||
| Official Date: | 1 January 2007 | ||||
| Dates: |
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| Volume: | Vol.26 | ||||
| Number: | No.1 | ||||
| Number of Pages: | 7 | ||||
| Page Range: | pp. 136-142 | ||||
| DOI: | 10.1021/om0607649 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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