Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral lewis acid
Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral lewis acid
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DOI：
10.1021/ja0523284
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发表时间：
2005-08-31
影响因子：
15
通讯作者：
Maruoka, K
中科院分区：
文献类型：
--
作者：
Kano, T;Hashimoto, T;Maruoka, K
μ-氧代型手性双钛（IV）氧化物（S，S）-1可成功地用于不同硝酮2与丙烯醛之间的不对称1，3-偶极环加成反应，得到了高至优异的对映选择性的异恶唑烷.例如，硝酮2（R =t-Bu）和丙烯醛在10 mol %的双-Ti（IV）催化剂（S，S）-1存在下，在二氯甲烷中于−40 °C反应，得到相应的内环加成物，ee值为97%。
A μ-oxo-type chiral bis-Ti(IV) oxide (S,S)-1can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones2and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. For instance, the reaction between nitrone2(R =t-Bu) and acrolein in the presence of 10 mol % of bis-Ti(IV) catalyst (S,S)-1in dichloromethane at −40 °C gave the corresponding endo cycloadduct with 97% ee.