Research Summary:
We are interested in functionalizing calixarene and resorcinarene skeletons as ligands for transition metal catalyzed organic transformations, with the aim of developing new selective catalysts that can be used in synthetic organic chemistry.

Research Descri ption:

Calix[4]arenes: Our work is focused on developing new methods for the synthesis of inherently chiral calix[4]arenes, which have potential use as asymmetric ligands in organic transformations (analogous to planar chiral ferrocenes).

Resorcinarenes: Our interest is in developing the resorcinarene skeleton for use in organic catalytic transformations by developing new bidentate ligands that have a defined shape. The key interest is in developing methodology to synthesize and derivatise these compounds, eventually moving into the area of asymmetric catalysis by tailoring an inherently chiral resorcinarene.

Selected Publications:

• Herbert, S.; Arnott, G. “Synthesis of Inherently Chiral Calix[4]arenes: Stereocontrol through Ligand Choice” Org. Lett. 2010, 12, 4600-4603
• Kleinhans, D.; Arnott, G. "Transient chirality in a distal-substituted resorcinarene metal complex" Dalton Trans. 2010, 39, 5780-5782
• Herbert, S.; Arnott, G. "An Asymmetric Ortholithiation Approach to Inherently Chiral Calix[4]arenes" Org Lett. 2009, 11, 4986-4989
• Arnott, G.; Brice, H.; Clayden, J.; Blaney, E. “Electrophile-induced dearomatising spirocyclisation of N-aryl isonicotinamides: a route to spirocyclic piperidines” Org Lett. 2008, 10, 3089-3092
• Arnott, G; Clayden, J; Hamilton, SD; “Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives.” Org. Lett. 2006, 8, 5325-5328
• Arnott, G; Hunter, R; “Enantioselective addition of diethylzinc to benzaldehyde catalysed by chiral, bridged resorcinarenes: a stereoselectivity model based on chirality transfer.” Tetrahedron 2006, 62, 992-1000
• Arnott, G; Hunter, R; Su, H; “Synthesis and characterization of chiral, bridged resorcinarenes as templates for asymmetric catalysis.” Tetrahedron 2006, 62, 977-991
• Arnott, G; Hunter, R; Mbeki, L; Mohamed, E; “New methodology for 2-alkylation of 3-furoic acids: application to the synthesis of tethered UC-781/d4T bifunctional HIV reverse-transcriptase inhibitors.” Tetrahedron Lett. 2005, 4023-4026
• Arnott, G; Page, PCB; Heaney, H; Hunter, R; “Synthesis of the first chiral, functionalised-bridged resorcinarenes in asymmetric catalysis: Evidence for intracavity asymmetric catalysis.” Eur. J. Org. Chem. 2004, 5126-5134
• Arnott, G.; Page, P. C. B.; Heaney, H.; Hunter, R.; Sampler, E. P. “Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes.” Synlett 2001, 3, 412-414