Song Jun, Wang Yi, Deng Li
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
J Am Chem Soc. 2006 May 10;128(18):6048-9. doi: 10.1021/ja060716f.
We describe the first efficient, direct asymmetric Mannich reactions with malonates and N-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 beta-ketoesters. The synthetic value of this new reaction is demonstrated in the establishment of a convergent enantioselective route toward the biologically important beta-amino acids under mild and air- and moisture-tolerant conditions.
我们描述了首例通过具有硫脲官能团的金鸡纳生物碱进行协同氢键催化,实现丙二酸酯与N - Boc芳基和烷基亚胺的高效、直接不对称曼尼希反应。我们还将该反应的适用范围扩展到了β - 酮酯。在温和且耐空气和湿气的条件下,通过建立一条汇聚式对映选择性路线来合成具有生物学重要性的β - 氨基酸,证明了这一新反应的合成价值。