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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Efficient asymmetric synthesis of alpha-alkylated 1, 4-cyclohexanedione derivatives, important chiral building blocks in the synthesis of natural products.

Alkylation of 1,4-cyclohexanedione monoethylene acetal SAMP-hydrazone with various electrophiles (10 examples given) and subsequent cleavage of the hydrazones with saturated oxalic acid furnished highly enantiomerically enriched alpha-alkylated mono-protected 1,4-cyclohexanedione derivatives in high yields and enantiomeric excesses of ee = 28, 80->/=99%. Reduction of the ketones gave the corresponding alcohols in good yields with high enantiomeric excesses (ee = 80->/=98%) and cis/trans-ratios of usually 85:15.[1]

References

  1. Efficient asymmetric synthesis of alpha-alkylated 1, 4-cyclohexanedione derivatives, important chiral building blocks in the synthesis of natural products. Enders, D., Nühring, A., Runsink, J. Chirality. (2000) [Pubmed]
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