| 12/01/2012: |
Congratulations to Nathan for his publication in Org Lett
The Ireland-Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important ß,ß’-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
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| 24/11/2011: |
Congratulations to Wes for his publication in OBC
α-Alkyl ß-amino esters are available in high diastereoselectivity through a silicon-free Claisen enolate [3,3]-sigmatropic rearrangement of enamide esters. Optimisation studies have probed the crucial role of the initial enolisation and the nature of the enamide N-centre. The demonstration of chirality transfer and the formation of ß-proline systems, is also presented.
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| 02/09/2011: |
Congratulations to Jim for his publication in Tetrahedron Lett
The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.
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| 25/03/2011: |
Congratulations to Dr Wesley Harker for passing his viva! |
| 28/02/2011: |
Nathan and Matt were both accepted onto AstraZeneca's Medicinal and Process Chemistry Workshop |
| 08/02/2011: |
Congratulations to Matt for his publication in Org Lett
The design, synthesis and study of a helical dialkylaminopyridine Lewis base catalyst has been reported in Organic Letters. The Helical DMAP analogue is based upon a helicenoid structure and displays good to excellent levels of selectivity (S ≤ 116) in the kinetic resolution of chiral secondary alcohols. The catalyst displays excellent reactivity with exceptionally low loadings of 0.05 mol % effecting practical levels of selectivity in kinetic resolutions. |
| 06/12/2010: |
The group's work was highlighted by ACS in their Noteworthy Chemistry Section.
This recognition was for the construction of biologically important amino esters through the use of an Ireland-Claisen rearrangement of alkyl-oxy and aryloxy-substituted allyl glycinates producing direct, stereocontrolled access to syn-ß-alkoxy and ß-aryloxy a-amino acid systems |
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