exo-selective asymmetric Diels-Alder reaction catalyzed by diamine salts as organocatalysts
exo-selective asymmetric Diels-Alder reaction catalyzed by diamine salts as organocatalysts
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DOI：
10.1002/asia.200700122
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发表时间：
2007-01-01
影响因子：
4.1
通讯作者：
Maruoka, Keiji
中科院分区：
文献类型：
--
作者：
Kano, Taichi;Tanaka, Youhei;Maruoka, Keiji
由联萘基取代的二胺和三氟甲磺酸形成的有机催化剂在α，β-不饱和醛与环戊二烯的Diels-Alder反应中表现出前所未有的外型选择性水平。一种新的轴向手性二胺也被设计为该反应的不对称变体的有机催化剂，其中所需的环加合物形成具有高的非对映体和对映体选择性。在巴豆醛与环戊二烯的不对称Diels-Alder反应中，观察到的最高非对映选择性大于20：1，有利于外环加合物。
An organocatalyst formed from a binaphthyl-substituted diamine and trifluoromethanesulfonic acid exhibited unprecedented levels of exo selectivity in the Diels-Alder reaction of alpha,beta-unsaturated aldehydes with cyclopentadiene. A novel axially chiral diamine was also designed as an organocatalyst for an asymmetric variant of this reaction, in which the desired cycload-ducts were formed with high diastereo- and enantioselectivities. The highest diastereoselectivity observed was greater than 20:1 in favor of the exo cycloadduct in the asymmetric Diels-Alder reaction of crotonaldehyde with cyclopentadiene.