A 4-hydroxypyrrolidine-catalyzed mannich reaction of aldehydes: control of anti-selectivity by hydrogen bonding assisted by Brønsted acids.
A 4-hydroxypyrrolidine-catalyzed mannich reaction of aldehydes: control of anti-selectivity by hydrogen bonding assisted by Brønsted acids.
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4-羟基吡咯烷催化的醛曼尼希反应：通过布朗斯台德酸辅助的氢键控制反选择性。
DOI：
10.1002/chem.200903537
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发表时间：
2010
期刊：
影响因子：
--
通讯作者：
I. Velilla
中科院分区：
文献类型：
--
作者：
E. Gómez;M. Maestro;A. Mielgo;Itziar Otazo;C. Palomo;I. Velilla
用4-羟基吡咯烷与外加Brnsted酸进行了醛与N-磺酰亚胺的反选择性Mannich反应。催化剂的设计基于三个元素：吡咯烷的α-取代基、4-羟基和Brnsted酸，它们的组合对于高化学和立体化学效率是必不可少的。该反应适用于芳香醛衍生的亚胺，这在以前报道的基于烯胺的反Mannich反应中很少使用。此外，N-对甲苯磺酰亚胺和N-诺酰亚胺都可以成功地使用，Mannich加合物很容易被还原或氧化，经过N-脱保护后，可以以良好的产率得到相应的β-氨基酸和β-氨基醇。实验结果还表明，该三元催化体系可用于其它烯胺类反应。
An anti-selective Mannich reaction of aldehydes with N-sulfonyl imines has been developed by using a 4-hydroxypyrrolidine in combination with an external Brønsted acid. The catalyst design is based on three elements: the alpha-substituent of the pyrrolidine, the 4-hydroxy group, and the Brønsted acid, the combination of which is essential for high chemical and stereochemical efficiency. The reaction works with aromatic aldehyde-derived imines, which have rarely been employed in previously reported enamine-based anti-Mannich reactions. Additionally, both N-tosyl and N-nosyl imines can be successfully used and the Mannich adducts can be easily reduced or oxidized, and after N-deprotection the corresponding beta-amino acids and beta-amino alcohols can be obtained with good yields. The results also show that this ternary catalytic system may be practical in other enamine-based reactions.
影响因子：
15
作者：
Sakthivel, K;Notz, W;Barbas, CF
通讯作者：
Barbas, CF
影响因子：
15
作者：
Mitsumori, S;Zhang, H;Barbas, CF
通讯作者：
Barbas, CF