Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.
Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.
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DOI：
10.1021/ja1071509
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发表时间：
2010-11-10
影响因子：
15
通讯作者：
Dong G
中科院分区：
文献类型：
--
作者：
Trost BM;Osipov M;Dong G
我们报道了含氮杂环化合物在钯催化的乙烯基氮杂环丙烷的动态动力学不对称烷基化反应中的亲核作用。得到的烷基化产物具有高的区域，化学和对映选择性。取代的1H-吡咯和1H-吲哚都成功地用于只得到支链N-烷基化产物。通过将该方法应用于制备几种药物化学先导化合物和溴吡咯生物碱（包括长酰胺B、长酰胺B甲酯、hanishin、agesamides A和B以及cyclooroidin），证明了该方法的合成实用性。
We report that nitrogen heterocycles can serve as competent nucleophiles in the palladium-catalyzed dynamic kinetic asymmetric alkylation of vinyl aziridines. The resulting alkylated products were obtained with high regio-, chemo-, and enantioselectivity. Both substituted 1H-pyrroles and 1H-indoles were successfully employed to give exclusively the branched N-alkylated products. The synthetic utility of this process was demonstrated by applying this method to the preparation of several medicinal chemistry lead compounds and bromopyrrole alkaloids including longamide B, longamide B methyl ester, hanishin, agesamides A and B, and cyclooroidin.
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影响因子：
16.6
作者：
Seiple, Ian B.;Su, Shun;Young, Ian S.;Lewis, Chad A.;Yamaguchi, Junichiro;Baran, Phil S.
通讯作者：
Baran, Phil S.
影响因子：
16.6
作者：
Bandini, Marco;Eichholzer, Astrid;Umani-Ronchi, Achille
通讯作者：
Umani-Ronchi, Achille
DOI：
10.1039/c39930001305
发表时间：
1993-08-21
影响因子：
--
作者：
DAMBROSIO, M;GUERRIERO, A;PIETRA, F
通讯作者：
PIETRA, F
影响因子：
1.8
作者：
Patel, Jignesh;Pelloux-Leon, Nadia;Vallee, Yannick
通讯作者：
Vallee, Yannick
影响因子：
1.8
作者：
Fattorusso, E;Taglialatela-Scafati, O
通讯作者：
Taglialatela-Scafati, O