使用手性膦 - 铜配合物对由N - 亚烷基甘氨酸酯生成的甲亚胺叶立德进行分子外环化和对映选择性环加成反应。
exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes.
作者信息
Oderaotoshi Yoji, Cheng Wenji, Fujitomi Shintaro, Kasano Yukihiro, Minakata Satoshi, Komatsu Mitsuo
机构信息
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
出版信息
Org Lett. 2003 Dec 25;5(26):5043-6. doi: 10.1021/ol036076s.
High diastereo- and enantioselectivities were obtained for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides generated from N-alkylideneglycine esters with dipolarophiles using chiral phosphine-copper complexes as catalysts. Whereas the cycloaddition of azomethine ylides catalyzed by metal salts generally afforded endo-adducts as the predominant product, the present method is the first example of an exo-selective cycloaddition. [reaction: see text]
使用手性膦 - 铜配合物作为催化剂，由N - 亚烷基甘氨酸酯生成的甲亚胺叶立德与亲偶极体进行不对称1,3 - 偶极环加成反应，可获得高的非对映选择性和对映选择性。虽然金属盐催化的甲亚胺叶立德环加成反应通常以生成内型加合物作为主要产物，但本方法是首例外型选择性环加成反应。[反应：见正文]
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