Phosphine-Catalyzed (3+2) Annulation of δ-Acetoxy Allenoates with 2-Sulfonamidomalonate: Synthesis of Highly Substituted 3-Pyrrolines and Mechanistic Insight

被引：31
|
作者：
Wang, Dong [1 ]
Liu, Wei [1 ]
Hong, Yang [1 ]
Tong, Xiaofeng [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 16期
关键词：
RING-CLOSING METATHESIS; NITROGEN-HETEROCYCLES; CHIRAL PHOSPHINES; N-TOSYLIMINES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ACTIVATED ALLENES; FACILE ENTRY; IMINES; CYCLOADDITION;
D O I：
10.1021/acs.orglett.8b02156
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and efficient synthetic protocol for 3-pyrrolines via the phosphine-catalyzed (3 + 2) annulation of (delta-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.
引用
收藏
页码：5002 / 5005
页数：4
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