膦催化 δ-乙酰氧基烯炔酸酯与 2-磺酰胺基丙二酸二乙酯的（3 + 2）环加成反应：高取代 3-吡咯啉的合成及机理研究。
Phosphine-Catalyzed (3 + 2) Annulation of δ-Acetoxy Allenoates with 2-Sulfonamidomalonate: Synthesis of Highly Substituted 3-Pyrrolines and Mechanistic Insight.
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , 1 Gehu Road , Changzhou , 213164 , China.
出版信息
Org Lett. 2018 Aug 17;20(16):5002-5005. doi: 10.1021/acs.orglett.8b02156. Epub 2018 Aug 9.
A mild and efficient synthetic protocol for 3-pyrrolines via the phosphine-catalyzed (3 + 2) annulation of δ-acetoxy allenoates with 2-sulfonamidomalonate is reported. The asymmetric version (up to 83% ee) is also achieved by using phosphine ( R)-SITCP as the catalyst. Mechanistic experiments disclose that the involved deprotonation of amide N-H and aza-addition to vinyl phosphonium might proceed in a concerted manner.
本文报道了一种通过膦催化δ-乙酰氧基烯炔酸盐与 2-磺酰胺基丙二酸二乙酯的（3 + 2）环加成反应合成 3-吡咯啉的温和高效的合成方法。使用手性膦 (R)-SITCP 作为催化剂，也可以实现不对称版本（高达 83%ee）。机理实验表明，酰胺 N-H 的去质子化和氮杂加成到乙烯基膦可能以协同的方式进行。
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