Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis
Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis
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DOI：
10.1002/chem.201501044
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发表时间：
2015-06-01
影响因子：
4.3
通讯作者：
Vicario, Jose L.
中科院分区：
文献类型：
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作者：
Sanchez-Diez, Eduardo;Fernandez, Maitane;Vicario, Jose L.
采用手性n -杂环卡宾（NHC）作为催化剂，建立了醛类和炔类之间对映选择性苯并酮反应的简单方法。在优化的反应条件下，这些炔酮与催化生成的Breslow中间体进行了干净和选择性的1,2加成反应，没有观察到竞争性steter型反应产生的任何副产物。该方法可以制备叔炔基甲醇作为高度富集对映体的材料，在有机合成中作为手性构件具有显著的潜力。
A straightforward procedure to carry out the enantioselective benzoin reaction between aldehydes and ynones by employing a chiral N-heterocyclic carbene (NHC) as catalyst was developed. Under the optimized reaction conditions, these ynones undergo a clean and selective 1,2-addition with the catalytically generated Breslow intermediate, not observing any byproduct arising from competitive Stetter-type reactivity. This procedure allows the preparation of tertiary alkynyl carbinols as highly enantioenriched materials, which have the remarkable potential to be used as chiral building blocks in organic synthesis.