Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.
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DOI:
10.1039/c4cc00394b
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发表时间:
2014-03-25
期刊:
Chemical communications (Cambridge, England)
影响因子:
--
通讯作者:
Wolf C
Wolf C
中科院分区:
其他
文献类型:
--
作者:
Cook AM;Wolf C

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本文首次报道了脂肪醛和芳香醛对双甘酰亚胺的催化不对称加成反应。该反应提供了前所未有的获得不同家族的N-取代的炔丙醇的途径,所述炔丙醇在10摩尔%的三氟甲磺酸锌和N-甲基麻黄碱的存在下以高产率和ee获得。非极性溶剂混合物的使用对于避免产物外消旋化和优化ee而不损害转化率是必不可少的。
The first catalytic asymmetric addition of ynamides to aliphatic and aromatic aldehydes is described. This reaction provides unprecedented access to a diverse family of N-substituted propargylic alcohols that are obtained in high yield and ee in the presence of 10 mol% of zinc triflate and N-methylephedrine The use of apolar solvent mixtures is essential to avoid product racemization and to optimize ee’s without compromising conversion.
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