Journal
CHEMICAL SCIENCE
Volume 6, Issue 4, Pages 2366-2370Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc03726j
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Funding
- Australian Research Council [DP120101315, FT110100319]
- Australian Research Council [FT110100319] Funding Source: Australian Research Council
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N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes. The reaction proceeds in good to excellent yield, and in cases that provide 2,2'-biaryls, enantioselectivity is observed. Mechanistic studies demonstrate the intermediacy of a cyclohexenyl beta-lactone, while implicating formation of the homoenolate as turnover limiting.
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