Pd(OAc)2-catalyzed cyclization of 2,3-allenoic acids in the presence of terminal α,β-unsaturated alkynones:: A one-pot highly stereoselective synthesis of 4-(3′-Oxo-1′(E)-alkenyl)-2(5H)-furanones

被引：14

作者：

Chen, Guofei ^{[1
]}

Zeng, Rong ^{[1
]}

Gu, Zhenhua ^{[2
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

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

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 19期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/ol801610w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd(OAc)(2)-catalyzed cyclization reaction of 2,3-allenoic acids in the presence of terminal alpha,beta-unsaturated alkynones afforded an E/Z mixture of 4-(3'-oxo-1'-alkenyl)-2(5H)-furanones. A subsequent complete isomerization of the Z-isomer to E-isomer was observed in DMSO at 90 degrees C, which led to a highly stereoselective synthesis of 4-(3'-oxo-1'(E)-alkenyl)-2(5H)-furanones. A possible mechanism is proposed.

引用

页码：4235 / 4238

页数：4

共 58 条

[1]

Alcaide B, 2002, CHEM-EUR J, V8, P1719, DOI 10.1002/1521-3765(20020402)8:7<1719::AID-CHEM1719>3.0.CO

[2]

2-U

[3] Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].

Alcaide, Benito ;

Almendros, Pedro ;

del Campo, Teresa Martinez .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687

[4] Allene substitution-controlled switching of dimerization to cycloisomerization in the PdII-catalyzed reaction of terminal α-allenones [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (17) :2844-2849

[5] Reaction of two different α-allenols in a heterocyclization/cross-coupling sequence:: Convenient access to functionalized buta-1,3-dienyl dihydrofurans [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (27) :4501-4504

[6] Divergent synthetic strategy leading to structurally diverse pyrrolidines and piperidines from common γ-aminoalkyl butenolide and aldehyde precursors [J].

Aurrecoechea, Jose M. ;

Suero, Ruben ;

de Torres, Esther .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8767-8778

[7] BASIDIFFERQUINONE ANALOGS, BASIDIFFERQUINONE-B AND BASIDIFFERQUINONE-C, WHICH INDUCE FRUITING-BODY FORMATION OF A BASIDIOMYCETE, FAVOLUS-ARCULARIUS [J].

AZUMA, M ;

YOSHIDA, M ;

HORINOUCHI, S ;

BEPPU, T .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (02) :344-345

[8] Dimerization of butenolide structures.: A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)-biepiasterolide [J].

Bagal, SK ;

Adlington, RM ;

Baldwin, JE ;

Marquez, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (26) :9100-9108

[9] A novel three-component butenolide synthesis [J].

Beck, B ;

Magnin-Lachaux, M ;

Herdtweck, E ;

Dömling, A .

ORGANIC LETTERS, 2001, 3 (18) :2875-2878

[10] NEW ROUTE TO LINEAR, POLYCYCLIC, SUBSTITUTED AROMATICS - DIELS-ALDER REACTIONS OF BICYCLIC DIMETHOXYCYCLOBUTENES [J].

BOECKMAN, RK ;

DELTON, MH ;

NAGASAKA, T ;

WATANABE, T .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (17) :2946-2948

← 1 2 3 4 5 6 →