Gott, Andrew L., Coles, Stuart R., Clarke, Adam J., Clarkson, Guy J. and Scott, Peter, P.. (2007) Chiral alkoxide-functionalized guanidinates from ring-opening rearrangement of aminooxazolinate complexes. Organometallics, Vol.26 (No.1). pp. 136-142. ISSN 0276-7333

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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
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry Faculty of Science > WMG (Formerly the Warwick Manufacturing Group)
Journal or Publication Title:	Organometallics
Publisher:	American Chemical Society
ISSN:	0276-7333
Date:	1 January 2007
Volume:	Vol.26
Number:	No.1
Number of Pages:	7
Page Range:	pp. 136-142
Identification Number:	10.1021/om0607649
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
URI:	http://wrap.warwick.ac.uk/id/eprint/32550

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