钌卟啉催化的三组分偶联反应用于多官能化吡咯啉的不对称合成。
Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction.
作者信息
Xu Hai-Wei, Li Gong-Yong, Wong Man-Kin, Che Chi-Ming
机构信息
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 354 Feng Lin Road, Shanghai 200032, China.
出版信息
Org Lett. 2005 Nov 24;7(24):5349-52. doi: 10.1021/ol050819n.
[reaction: see text] Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).
[反应：见正文] 通过钌卟啉催化的三组分偶联反应合成了手性多官能化吡咯啉。在一锅反应中，钌卟啉催化由手性重氮酯和亚胺原位生成手性甲亚胺叶立德。手性甲亚胺叶立德与亲偶极体的不对称1,3-偶极环加成反应以良好的产率和高非对映选择性（高达92%的非对映体过量）得到相应的吡咯啉。
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