Copper(I)-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals for the synthesis of versatile alkaloid precursors.
Copper(I)-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals for the synthesis of versatile alkaloid precursors.
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DOI：
10.1021/ja308872z
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发表时间：
2012-10
影响因子：
15
通讯作者：
Shi‐Liang Shi;Xiao-Feng Wei;Yohei Shimizu;M. Kanai
中科院分区：
文献类型：
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作者：
Shi‐Liang Shi;Xiao-Feng Wei;Yohei Shimizu;M. Kanai
发展了一种通用的催化对映选择性方法，该方法可以从稳定且容易获得的环状半缩醛和环状酮出发，制备具有各种酮部分的五元、六元和七元N-杂环。该方法包括三个连续的步骤，在一锅（羟醛加成，脱水，和对映选择性分子内氮杂迈克尔反应），所有这些都是由手性铜（I）共轭布朗斯台德碱催化剂促进。该方法可用于快速获得用于合成药物先导生物碱的通用手性结构单元。
A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition, dehydration, and enantioselective intramolecular aza-Michael reaction), all of which are promoted by a chiral copper(I)-conjugated Brønsted base catalyst. This method is useful for rapid access to versatile chiral building blocks for the synthesis of drug-lead alkaloids.