Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes

被引：0
|
作者：
Bakthadoss, Manickam [1 ]
Mushaf, Mohammad [1 ]
Agarwal, Vishal [1 ]
Reddy, Tadiparthi Thirupathi [1 ]
Sharada, Duddu S. [2 ]
机构：
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
[2] Indian Inst Technol, Dept Chem, Hyderabad 502285, Telangana, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 04期
关键词：
1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDES; RING-SYSTEM; DERIVATIVES; CONSTRUCTION; CARBONYL;
D O I：
10.1039/d1ob02042k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the synthesis of tricyclic pyrrolidinochromenes has been developed via an intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated in situ from 1,3-dienyl ester tethered O-hydroxyarylaldehyde and glycine esters. The reaction is highly regio- and diastereoselective in nature and provided the potentially bioactive pyrrolidine fused tricyclic cycloadducts in excellent yields with wide substrate scope. Interestingly this reaction constructs two rings and four contiguous stereogenic centers in which one of them is an all carbon quaternary center in a unique fashion.
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收藏
页码：778 / 782
页数：5
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