Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction
Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction
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DOI：
10.1021/ja9072194
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发表时间：
2009-11-18
影响因子：
15
通讯作者：
Yudin, Andrei K.
中科院分区：
文献类型：
--
作者：
Hili, Ryan;Yudin, Andrei K.
两性氨基醛以稳定的二聚体形式存在，与α， β -不饱和醛发生aza-Michael/aldol多米诺骨牌反应，以高产率和非对映选择性提供稳定的1,5-氨基羟基醛。反应结果取决于两性氨基醛的二聚体性质以及反应过程中NH叠氮啶和两醛官能团之间的正交性。通过使用不利于二聚体解离的反应条件，aza-Michael过程被导向了一种新的8-（烯烯醛）-外三角环化。本文所描述的结果进一步证明了两性分子在反应发现中的潜力。
Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.