Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid

[摘要] The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, a readily derived α-iodoenone participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones are useful, enantiomerically pure building blocks for organic synthesis.

[学科分类] 精神健康和精神病学

[关键词] 1;2-addition;α;β-annulation;cross-coupling;cyclohexenone;enantiomerically pure;α-iodination;quinic acid