Organocopper chemistry of quinone bisketals. Application to the synthesis of isoprenoid quinone systems

BL Chenard, MJ Manning, PW Raynolds…

文献索引：Chenard, Bertrand L.; Manning, Michael J.; Raynolds, Peter W.; Swenton, John S. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 378 - 384

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被引用次数: 31

摘要

We report here the chemistry of lithium organocuprates of quinone bisketals. These reagents react efficiently (transfer of greater than one R group of R&uLi) with allylic bromides to afford high yields of functionalized bisketals. The reaction of these cuprates with acid chlorides is acceptable for synthetic purposes while conjugate additions to cyclohexenone are of little value. This chemistry has been applied to the synthesis of 4a, menaquinone-2 (4b), 6b ...