Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

被引：9
作者：
Huang, Huan-Ming [1 ]
He, Qiong [1 ]
Procter, David J. [1 ]
机构：
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
来源：
SYNLETT | 2020年 / 31卷 / 01期
基金：
英国工程与自然科学研究理事会;
关键词：
radical relay; catalysis; samarium diiodide; cascade reaction; cyclization; ELECTRON-TRANSFER REDUCTION; DOMINO REACTIONS; DERIVATIVES;
D O I：
10.1055/s-0039-1690196
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
SmI2-catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.
引用
收藏
页码：45 / 50
页数：6
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