Enantioselective Synthesis of α-Allyl-α-aryldihydrocoumarins and 3-lsochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

被引：33

作者：

Akula, Ramulu ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Synth & Solid State Pharmaceut Ctr SSPC, Dublin 4, Ireland

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 21期

基金：

爱尔兰科学基金会;

关键词：

RADICAL-MEDIATED ALLYLATION; TSUJI ALLYLATION; ENOL CARBONATES; ARYL KETONES; CONSTRUCTION; IDENTIFICATION; ISOFLAVANONES;

D O I：

10.1021/acs.orglett.6b02584

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective Pd-catalyzed DAAA of alpha-aryl-beta-oxo esters has been developed employing the (R,R)-ANDEN-phenyl Trost ligand to prepare a series of alpha-aryl-alpha-allyldihydrocoumarins and 3-isochromanones. A variety of aryl groups were successfully employed to afford the dihydrocoumarin and 3-isochromanone products in high yields up to 95% and ee's up to 96%. Under these conditions, substrates containing di- and mono-ortho-substituted aryl groups gave the highest levels of enantioselectivities. This work represents the first example of the enantioselective preparation of all-carbon quaternary alpha-allyl-alpha-aryl dihydrocoumarins and 3-isochromanones.

引用

页码：5472 / 5475

页数：4

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