Cyclopentane-1,2-dione bis(tert-butyldimethylsilyl) enol ether in asymmetric organocatalytic Mukaiyama-Michael reactions

被引：5

作者：

Reile, Indrek ^{[1
]}

Paju, Anne ^{[1
]}

Kanger, Tonis ^{[1
]}

Jaerving, Ivar ^{[1
]}

Lopp, Margus ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem, EE-19086 Tallinn, Estonia

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 12期

关键词：

Mukaiyama-Michael reaction; Organocatalysis; Cyclopentane-1,2-dione; Cyclopentane-1,2-dione bis(tert-butyldimethylsilyl) enol ether; alpha; beta-Unsaturated aldehyde; OXIDATIVE RING-CLEAVAGE; ENANTIOSELECTIVE SYNTHESIS; GAMMA-LACTONE; 3-ALKYL-1,2-CYCLOPENTANEDIONES; ALDEHYDES;

D O I：

10.1016/j.tetlet.2012.01.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopentane-1,2-dione bis(tert-butyldimethylsilyl) enol ether readily undergoes organocatalytic reactions with alpha,beta-unsaturated aldehydes resulting in Mukaiyama-Michael adducts which, after reduction of the aldehyde group and deprotection result in chiral 1,2-diketones (in mono-enolic form) in good yields (up to 66%) and with high stereoselectivity (up to 94% ee). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1476 / 1478

页数：3

共 6 条

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[4] Enantioselective Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates
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[5] Solvent-free Mukaiyama and Mukaiyama-Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases
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[6] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
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