Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines

Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines
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DOI:
10.1002/anie.201100706
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发表时间:
2011-01-01
影响因子:
16.6
通讯作者:
Zhu, Jieping
Zhu, Jieping
中科院分区:
化学1区
文献类型:
--
作者:
Denis, Jean-Baptiste;Masson, Geraldine;Zhu, Jieping

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N-磺酰亚胺(I)和(IV)与联烯酸酯(II)的不对称缩甲醛[2 + 2]环加成反应由双官能的含甘氨酰胺的奎尼丁有机催化剂有效地催化,分别得到氮杂环丁烷(III)和(V),对映选择性高达98%e.。
Asymmetric formal [2 + 2] cycloaddition of N‐sulfonylimines (I) and (IV) with allenoates (II) is efficiently catalyzed by a bifunctional glycinamide‐containing quinidine organocatalyst to give azetidines (III) and (V), resp., in high enantioselectivity (up to 98% e.e.).