Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes

被引:267
作者
Zhu, Rong [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院;
关键词
HIGHLY EFFICIENT SYNTHESIS; ABSOLUTE RATE CONSTANTS; BETA-KETO-ESTERS; ASYMMETRIC BROMOLACTONIZATION; STEREOSELECTIVE-SYNTHESIS; KINETIC CHARACTERISTICS; OXIDATIVE OXYARYLATION; ALLYLIC ACYLOXYLATION; PHOTOREDOX CATALYSIS; UNACTIVATED ALKENES;
D O I
10.1021/jacs.5b04821
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A versatile method for the rapid synthesis of diverse enantiomerically enriched lactones has been developed based on Cu-catalyzed enantioselective radical oxyfunctionalization of alkenes. The scope of this strategy encompasses a series of enantioselective difunctionalization reactions: oxyazidation, oxysulfonylation, oxyarylation, diacyloxylation, and oxyalkylation. These reactions provide straightforward access to a wide range of useful chiral lactone building blocks containing tetrasubstituted stereogenic centers, which are hard to access traditionally.
引用
收藏
页码:8069 / 8077
页数:9
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