The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines
The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines
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DOI：
10.1021/jo981700d
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发表时间：
1998-12-25
影响因子：
3.6
通讯作者：
Pennell, AMK
中科院分区：
文献类型：
--
作者：
Adams, H;Anderson, JC;Pennell, AMK
在布朗斯台德酸的存在下，将烷基硝膦酸盐阴离子加成到PMB亚胺上，该亚胺衍生自苯甲醛或直链甲醛，产率大于90%，最高可达10：1的非对映选择有利于反式异构体。这个加成反应的机理是有趣的，正在调查中。中度不稳定的对硝基胺可以用二碘化钐还原，并用CAN除去PMB基团，以良好的总产率得到敏感的1，2-二胺，而不损害非对映选择性。该方案代表了一种新的，立体选择性合成某些1，2-二胺。
The addition of alkyl nitronate anions to PMB imines, derived from benzaldehyde or straight-chain carbaldehydes, in the presence of a Bronsted acid, proceeds in greater than 90% yield with up to 10:1 diastereoselection favoring the anti isomer. The mechanism of this addition reaction is intriguing and is under investigation. The moderately unstable p-nitro amines can be reduced with samarium diiodide and the PMB group removed with CAN, in good overall yields, to give sensitive 1,2-diamines without erosion of diastereoselectivity. This protocol represents a new, stereoselective synthesis of certain 1,2-diamines.