Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

被引：7

作者：

Fernandez, Marti ^{[1
,2
]}

Parera, Magda ^{[1
,2
]}

Parella, Teodor ^{[3
]}

Lledo, Agusti ^{[1
,2
]}

Le Bras, Jean ^{[4
]}

Muzart, Jacques ^{[4
]}

Pla-Quintana, Anna ^{[1
,2
]}

Roglans, Anna ^{[1
,2
]}

机构：

[1] Univ Girona, Inst Quim Computac & Catalisi, Campus Montilivi S-N, Girona 17071, Catalonia, Spain

[2] Univ Girona, Dept Quim, Campus Montilivi S-N, Girona 17071, Catalonia, Spain

[3] Univ Autonoma Barcelona, Serv Ressonancia Magnet Nucl, Cerdanyola Del Valles 08193, Catalonia, Spain

[4] Univ Reims, Inst Chim Mol Reims, CNRS, UMR 7312, BP 1039, F-51687 Reims 2, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 11期

关键词：

cycloaddition; diastereoselectivity; kinetic resolution; Morita-Baylis-Hillman adducts; rhodium; CARBON QUATERNARY STEREOCENTERS; ENANTIOSELECTIVE CONSTRUCTION; MACROCYCLIC SYSTEMS; KINETIC RESOLUTION; ALKYNES; HETEROCYCLES; 1,6-ENYNES; COMPLEXES; MOLECULES; CHEMISTRY;

D O I：

10.1002/adsc.201600039

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields.

引用

页码：1848 / 1853

页数：6

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