奎宁和奎尼丁的催化不对称全合成。
Catalytic asymmetric total syntheses of quinine and quinidine.
作者信息
Raheem Izzat T, Goodman Steven N, Jacobsen Eric N
机构信息
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
出版信息
J Am Chem Soc. 2004 Jan 28;126(3):706-7. doi: 10.1021/ja039550y.
PMID:14733531
Abstract
The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.
摘要
奎宁和奎尼丁的催化不对称合成在16步反应中实现。最近开发的salen(Al)催化的氰基乙酸甲酯对映选择性迈克尔加成反应用于构建关键的C4立体中心，对映体过量率为92%，后期的不对称双羟基化反应用于区分共同中间体，并以高选择性得到两种所需的非对映体产物。
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