Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes

被引：31

作者：

Sun, Ning ^{[1
]}

Chen, Ming ^{[1
]}

Liu, Yuanhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 09期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT SYNTHESIS; REGIOSELECTIVE OXIDATION; HIGHLY EFFICIENT; CYCLOISOMERIZATION REACTIONS; RAPID ACCESS; REARRANGEMENT; ESTERS; KETONES; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/jo500573s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to alpha-functionalized-alpha,beta-unsaturated ketones with excellent regio- and diastereocontrol via a regioselective attack of the N-oxide to the gold-activated alkyne followed by a 1,2-carbonate migration. In addition, the alkene products could be further transformed into the valuable 5-hydroxycyclopent-2-enones via cyclocondensation with acetone or cyclodimerization under basic conditions.

引用

页码：4055 / 4067

页数：13

共 83 条

[1] Acid-promoted reactions of butan-2,3-dione [J].

Alexandropoulou, I ;

Crabb, TA ;

Patel, AV ;

Hudec, J .

TETRAHEDRON, 1999, 55 (18) :5867-5874

[2] DIMERIZATION OF CYCLOPENTADIENONES [J].

ALLEN, CFH ;

VANALLAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) :5165-5167

[3] Gold-catalyzed addition of carbon nucleophiles to propargyl carboxylates [J].

Amijs, Catelijne H. M. ;

Opez-Carrillo, Veronica ;

Echavarren, Antonio M. .

ORGANIC LETTERS, 2007, 9 (20) :4021-4024

[4] Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].

Bhunia, Sabyasachi ;

Ghorpade, Satish ;

Huple, Deepak B. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942

[5] α-Diketones as acyl anion equivalents: a non-enzymatic thiamine-promoted route to aldehyde ketone coupling in PEG400 as recyclable medium [J].

Bortolini, Olga ;

Fantin, Giancarlo ;

Fogagnolo, Marco ;

Giovannini, Pier Paolo ;

Venturi, Valentina ;

Pacifico, Salvatore ;

Massi, Alessandro .

TETRAHEDRON, 2011, 67 (42) :8110-8115

[6]

Braunstein P., 1990, Inorg. Synth, V27, P218, DOI 10.1002/9780470132586.ch42

[7] Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].

Buzas, A ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (03) :515-518

[8] Gold-catalyzed rearrangement of propargylic tert-butyl carbonates [J].

Buzas, Andrea K. ;

Istrate, Florin M. ;

Gagosz, Fabien .

TETRAHEDRON, 2009, 65 (09) :1889-1901

[9] [(S)-BINAP]PdBr2-catalyzed direct synthesis of 2,3-disubstituted indoles via a tandem reaction between arylamines and α-diketones [J].

Cabrera, A. ;

Sharma, P. ;

Ayala, M. ;

Rubio-Perez, L. ;

Amezquita-Valencia, Manuel .

TETRAHEDRON LETTERS, 2011, 52 (50) :6758-6762

[10] A highly efficient ruthenium-catalyzed rearrangement of α,β-epoxyketones to 1,2-diketones [J].

Chang, CL ;

Kumar, MP ;

Liu, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2793-2796

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