Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes

被引：30

作者：

Andres, Jose M. ^{[1
]}

Losada, Jorge

Maestro, Alicia

Rodriguez-Ferrer, Patricia

Pedrosa, Rafael ^{[1
]}

机构：

[1] Univ Valladolid, Inst CINQUIMA, Fac Ciencias, Paseo Belen 7, E-47011 Valladolid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 16期

关键词：

1,3-DICARBONYL COMPOUNDS; STEREOCONTROLLED CONSTRUCTION; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; BIFUNCTIONAL THIOUREAS; ALDOL REACTION; AZA-HENRY; CATALYSTS; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/acs.joc.7b01177

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel supported chiral bifunctional squaramides have been easily prepared starting from diamines derived from natural amino acids and commercially available aminoalkyl polystyrene resins. These squaramides behave as excellent stereoselective recoverable organocatalysts in different Michael additions, in neat conditions at room temperature. The reaction on 2-(2-nitrovinyl) phenol as electrophile lead, in excellent yields and enantioselectivities, to intermediates that can be easily transformed into 4H-chromenes, and spirochromanones.

引用

页码：8444 / 8454

页数：11

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