Journal
CHEMICAL SCIENCE
Volume 5, Issue 2, Pages 602-607Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc52409d
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Funding
- EPSRC
- European Research Council (ERC) [246785]
- Marie Curie Fellowship program [274783]
- Bristol Chemical Synthesis DTC
- Mark Evans (Bristol Alumnus)
- Engineering and Physical Sciences Research Council [EP/I038071/1, 1114122, EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/K03927X/1, EP/I038071/1] Funding Source: UKRI
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Boron-ate complexes derived from enantioenriched secondary benzylic boronic esters and aryl lithiums have been reacted with quinolinium, pyridinium and dihydroisoquinolinium salts to give enantioenriched heterocyclic structures with very high diastereocontrol over two contiguous stereogenic centres (87: 1 3-99 : 1 dr; >95 : 5 es). The salts were derived from the corresponding heterocycle and Troc-Cl or dimethylTroc-Cl. In the case of the quinolinium and pyridinium salts, the presence of a 3-carboxyamide group increased both reactivity and diastereoselectivity. The unusually high diastereoselectivity observed is thought to originate from strong cation-p interactions between the cationic heterocycle and the electron rich benzylic boronate complex with minimisation of steric interactions between the substituents on the ate complex and the non-planar substituents on the heterocycle.
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