Synthesis ( IF 2.2 ) Pub Date : 2018-07-16 , DOI: 10.1055/s-0037-1610453 Wenling Qin 1 , Nan Zhang 1 , Yige Li 2 , Zhili Chen 1
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Abstract
Hemiaminals are common in natural products as well as bioactive compounds. Hemiaminals with an indole moiety are particularly attractive due to the significant bioactivity of indoles. Herein, we reported an efficient organocatalyzed indole N-1 nucleophilic addition of α-oxoaldehydes to deliver various indole hemiaminals in good yields (up to 92%) and excellent regioselectivities with DABCO or triethylamine as the catalyst. The method is characterized by mild reaction conditions, widely available reagents, and general substrate scope, and it is also applicable to late-stage transformations without affecting the hemiaminal group. In addition, we carried out this reaction in an enantioselective fashion in good yields and high ee values with two general substrates.
Hemiaminals are common in natural products as well as bioactive compounds. Hemiaminals with an indole moiety are particularly attractive due to the significant bioactivity of indoles. Herein, we reported an efficient organocatalyzed indole N-1 nucleophilic addition of α-oxoaldehydes to deliver various indole hemiaminals in good yields (up to 92%) and excellent regioselectivities with DABCO or triethylamine as the catalyst. The method is characterized by mild reaction conditions, widely available reagents, and general substrate scope, and it is also applicable to late-stage transformations without affecting the hemiaminal group. In addition, we carried out this reaction in an enantioselective fashion in good yields and high ee values with two general substrates.
中文翻译：
通过有机催化的亲核性将吲哚添加到醛中直接制备吲哚类化合物
摘要
在天然产物以及生物活性化合物中，常见的是半胱氨酸。由于吲哚具有显着的生物活性，具有吲哚部分的半乳糖特别有吸引力。本文中，我们报道了一种高效的有机催化的吲哚N-1亲核加成α-氧醛，以高收率（高达92％）和以DABCO或三乙胺为催化剂的出色的区域选择性来递送各种吲哚缩醛。该方法的特点是反应条件温和，试剂广泛，底物范围宽泛，并且还适用于后期转化而不影响半氨醛基团。另外，我们以对映选择性的方式以两种常规底物以高收率和高ee值进行了该反应。
在天然产物以及生物活性化合物中，常见的是半胱氨酸。由于吲哚具有显着的生物活性，具有吲哚部分的半乳糖特别有吸引力。本文中，我们报道了一种高效的有机催化的吲哚N-1亲核加成α-氧醛，以高收率（高达92％）和以DABCO或三乙胺为催化剂的出色的区域选择性来递送各种吲哚缩醛。该方法的特点是反应条件温和，试剂广泛，底物范围宽泛，并且还适用于后期转化而不影响半氨醛基团。另外，我们以对映选择性的方式以两种常规底物以高收率和高ee值进行了该反应。
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