Asymmetric counterion pair catalysis: An enantioselective Bronsted acid-catalyzed protonation
Asymmetric counterion pair catalysis: An enantioselective Bronsted acid-catalyzed protonation
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DOI：
10.1002/adsc.200800020
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发表时间：
2008-05-01
影响因子：
5.4
通讯作者：
Bats, Jan W.
中科院分区：
文献类型：
--
作者：
Rueping, Magnus;Theissmann, Thomas;Bats, Jan W.
发展了一种新的不对称Bronsted酸催化的级联反应，该反应包括1，4-加成、对映选择性质子化和1，2-加成。这种有机催化级联反应不仅首次在温和的反应条件下以较高的对映和对映选择性提供了3-和2，3-取代四氢喹啉和八氢吖啶的高产率，而且还是第一个在有机催化多米诺骨牌反应中手性Bronsted酸催化质子化反应的例子。此外，新的Bronsted酸催化的氢化物-质子-氢化物转移级联可用于在高效的一锅反应序列中制备最多具有三个新立体中心的新分子支架。
A new asymmetric Bronsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3- and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Bronsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Bronsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.