(R)-螺[4,5]癸-2,7-二酮的合成

Synthesis of Enantiomerically Pure (R)-Spiro4,5]decane-2,7decane-2,7-dione

从环己烯酮出发 ,经手性催化的Michael加成反应 ,Wolff重排反应延长碳链 ,再利用重氮化合物的C—H插入反应 ,以 8步反应 2 8 5 %的总收率合成了手性 β ,β′ 螺二酮 .在合成路线中手性中心的构型保持不变 .在最后的检测中未发现另一对映体 ,开始产生的手性中心在合成过程没有消旋化 .

Starting from cyclohexenone, through catalytic asymmetric Michael addition, homologation by Wolff rearrangement, and finally Rh(H) carbene intramolecular C-H insertion, the enantiornerically pure (R)-spiro[4,5]-decane-2,7-dione was synthesized in 8 steps and 28.5% overall yield. This synthesis further confirms that Rh(H) carbene C-H insertion proceeds with complete retention of configuration.