Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Bronsted base/thiourea bifunctional catalyst

被引：25

作者：

Antunez, Diego-Javier Barrios ^{[1
]}

Greenhalgh, Mark D. ^{[1
]}

Fallan, Charlene ^{[1
]}

Slawin, Alexandra M. Z. ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 30期

关键词：

INTRAMOLECULAR MICHAEL ADDITION; FRIEDEL-CRAFTS REACTION; ASYMMETRIC-SYNTHESIS; DIMETHYLSULFOXIDE SOLUTION; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; ALPHA-ARYLATION; CARBON ACIDS; THIOUREA; ORGANOCATALYSTS;

D O I：

10.1039/c6ob01326k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96 : 4 dr, 95 : 5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pro-nucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.

引用

页码：7268 / 7274

页数：7

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