Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

被引：3
|
作者：
Shah, Babar Hussain [1 ,2 ]
Khan, Sardaraz [1 ,2 ]
Zhao, Can [1 ,2 ]
Zhang, Yong Jian [1 ,2 ,3 ]
机构：
[1] Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[3] Shanghai Jiao Tong Univ, Sichuan Res Inst, Chengdu 610042, Sichuan, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期
基金：
中国国家自然科学基金;
关键词：
FORMAL 3+2 CYCLOADDITION; VINYLETHYLENE CARBONATES; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; BETA-KETOESTERS; DIHYDROFURANS; CONSTRUCTION; ALLYLATION; DITERPENES; ACCESS;
D O I：
10.1021/acs.joc.3c00976
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the enantioselective synthesisof 2,3-dihydrofuransbearing a quaternary stereocenter has been developed via Pd-catalyzedasymmetric allylic cycloaddition and a retro-Dieckmann Fragmentationcascade. The asymmetric allylic cycloaddition of vinylethylene carbonateswith 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentationproceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted2,3-dihydrofurans in high yields with excellent enantioselectivities.
引用
收藏
页码：12100 / 12104
页数：5
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