The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids
The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids
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DOI：
10.1021/ja060716f
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发表时间：
2006-05-10
影响因子：
15
通讯作者：
Deng, Li
中科院分区：
文献类型：
--
作者：
Song, Jun;Wang, Yi;Deng, Li
我们描述了第一个与丙二酸酯和N-叔丁氧羰基芳基和烷基亚胺通过与带有硫脲官能度的金鸡纳碱的协同氢键催化进行的有效、直接的不对称曼尼希反应。我们还将该反应的范围扩展到β-酮酯。这一新反应的合成价值体现在建立了一个收敛的对映选择性路线，在温和的和空气和潮湿的条件下，生物学上重要的β-氨基酸。
We describe the first efficient, direct asymmetric Mannich reactions with malonates andN-Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona alkaloid bearing a thiourea functionality. We have also extended the scope of this reaction to β-ketoesters. The synthetic value of this new reaction is demonstrated in the establishment of a convergent enantioselective route toward the biologically important β-amino acids under mild and air- and moisture-tolerant conditions.