The organocatalytic enantioselective [3+2] cycloaddition reaction of α,β-unsaturated aldehydes with azomethine ylides applied to the asymmetric synthesis of densely substituted pyrroloisoquinolines

被引：10
|
作者：
Iza, Ainara [1 ]
Ugarriza, Iratxe [1 ]
Uria, Uxue [1 ]
Reyes, Efraim [1 ]
Carrillo, Luisa [1 ]
Vicario, Jose L. [1 ]
机构：
[1] Univ Basque Country, Fac Ciencia & Tecnol, Dept Quim Organ 2, E-48080 Bilbao, Spain
来源：
TETRAHEDRON | 2013年 / 69卷 / 42期
关键词：
Cycloaddition; Dipolar reaction; Organocatalysis; Heterocycles; Pyrroloisoquinolines; POMERANZ-FRITSCH REACTION; ELECTROPHILIC CYCLIZATION; ISOQUINOLINE SYNTHESIS; ALKALOIDS; PATHWAYS;
D O I：
10.1016/j.tet.2013.08.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of densely functionalized pyrrolo[2,1-a]isoquinolines was accomplished using the organocatalytic [3+2] cycloaddition between enals and azomethine ylides under iminium catalysis developed in our group some years ago as the key step. The cycloaddition proceeds smoothly yielding the corresponding pyrrolidine as a single endo diastereoisomer with enantiopurity in the range of 94-96% and further manipulations of the obtained cycloadducts using high yielding reaction protocols and a final mesylation/intramolecular N-alkylation sequence allowed the synthesis of target compounds in which the integrity of all stereocenters installed during the first step is maintained. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8878 / 8884
页数：7
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