Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4+2] Cyclizations

被引：112

作者：

Gicquel, Maxime ^{[1
]}

Gomez, Catherine ^{[1
]}

Retailleau, Pascal ^{[1
]}

Voituriez, Arnaud ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] CNRS, Ctr Rech Gif, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

关键词：

BAYLIS-HILLMAN CARBONATES; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; DIELS-ALDER; FUNCTIONALIZED CYCLOPENTENES; ASYMMETRIC CATALYSIS; AMINO-ACID; ANNULATION; CONSTRUCTION; ALLENOATES;

D O I：

10.1021/ol401798w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphine promoted reactions between 3-arylideneoxindoles and (delta-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted (delta-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.

引用

页码：4002 / 4005

页数：4

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