Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones
Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones
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DOI：
10.1021/ja201794v
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发表时间：
2011-06-15
影响因子：
15
通讯作者：
Tian, Jin-Miao
中科院分区：
文献类型：
--
作者：
Chen, Zhi-Min;Zhang, Qing-Wei;Tian, Jin-Miao
以金鸡纳生物碱衍生物为催化剂，建立了一种新型的不对称卤化/半品那酚重排反应。合成了两种类型的β-卤代酮(X=溴、氯)，产率达95%，对映体过量达99%。β-卤代酮的(+)和(-)对映体很容易得到。
A novel asymmetric halogenation/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. Two types of beta-haloketones (X = Br, Cl) were obtained with up to 95% yield and 99% enantiomeric excess. The desired (+) and (-) enantiomers of the beta-haloketones were readily obtained.