Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles

被引：57

作者：

Afewerki, Samson ^{[1
,2
]}

Ma, Guangning ^{[1
]}

Ibrahem, Ismail ^{[1
]}

Liu, Leifeng ^{[2
,3
]}

Sun, Junliang ^{[2
,3
]}

Cordova, Armando ^{[1
,3
]}

机构：

[1] Mid Sweden Univ, Dept Nat Sci, SE-85170 Sundsvall, Sweden

[2] Stockholm Univ, Berzelii Ctr EXSELENT, SE-10691 Stockholm, Sweden

[3] Stockholm Univ, Dept Mat & Environm Chem, SE-10691 Stockholm, Sweden

来源：

ACS CATALYSIS | 2015年 / 5卷 / 02期

关键词：

asymmetric cocatalysis; alpha; beta-unsaturated aldehydes; dynamic transformations; polysubstituted; spirocyclic oxindoles; all-carbon quaternary stereocenter; TRANSITION-METAL; SYNERGISTIC CATALYSIS; ALLYLIC ALKYLATION; SPIROOXINDOLE DERIVATIVES; ALPHA-ALLYLATION; NATURAL-PRODUCTS; CONSTRUCTION; AMINE; COMBINATION; ALDEHYDES;

D O I：

10.1021/cs501975u

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070305 [高分子化学与物理];

摘要：

The highly enantioselective (up to >99.5:0.5 er) synthesis of polysubstituted spirocyclic oxindoles with four new contiguous stereocenters, including the spiro all-carbon quaternary center, is disclosed. It is accomplished by the highly stereoselective control of a dynamic conjugate/intramolecular allylic alkylation relay sequence based on the synergistic cooperation of metal and chiral amine catalysts in which the careful selection of organic Nand, metal complex, and chiral amine is essential. The intermolecular C-C bond-forming step occurred only when both the metal and chiral amine catalysts were present.

引用

页码：1266 / 1272

页数：7

共 91 条

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Direct Regiospecific and Highly Enantioselective Intermolecular a-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts [J].