Diversity in platinum-catalyzed hydrative cyclization of trialkyne substrates to form tetracyclic ketones

被引：28

作者：

Chang, Hsu-Kai ^{[1
]}

Liao, Yen-Chen ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 21期

关键词：

D O I：

10.1021/jo701458b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report a one-pot synthesis of tetracyclic ketones via PtI2-catalyzed hydrative cyclization of trialkyne functionalities. These triyne substrates bear an electron-rich aryl group at the outer alkyne to direct the initial hydration occurring at the adjacent alkynyl carbon. This tandem catalysis is proposed to comprise two alkyne hydrations, an alkyne insertion and an intramolecular aldol condensation.

引用

页码：8139 / 8141

页数：3

共 19 条

[1] PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones [J].

Chang, Hsu-Kai ;

Datta, Swarup ;

Das, Arindam ;

Odedra, Arjan ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4744-4747

[2] Ruthenium-catalyzed hydrative cyclization of 1,5-enynes [J].

Chen, YY ;

Ho, DM ;

Lee, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12184-12185

[3] The virtue of palladium-catalyzed domino reactions -: Diverse oligocyclizations of acyclic 2-bromoenynes and 2-bromoenediynes [J].

De Meijere, A ;

Von Zezschwitz, P ;

Bräse, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :413-422

[4] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].

Denmark, SE ;

Thorarensen, A .

CHEMICAL REVIEWS, 1996, 96 (01) :137-165

[5] Heterocycles by PtCl2 catalyzed intramolecular carboalkoxylation or carboamination of alkynes [J].

Fürstner, A ;

Davies, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15024-15025

[6] Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes [J].

Fürstner, A ;

Davies, PW ;

Gress, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8244-8245

[7] PtCl2-catalyzed rearrangement of methylenecyclopropanes [J].

Furstner, Alois ;

Aissa, Christophe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6306-6307

[8]

Hegedus L.S., 1999, TRANSITION METALS SY, V2nd

[9]

Ho T.-L., 1994, TACTICS ORGANIC SYNT, P79

[10] Metal-catalyzed chemoselective cycloisomerization of cis-2,4-dien-1-als to 3-cyclopentenones and 4-alkylidene-3,4-dihydro-2H-pyrans [J].

Lo, Ching-Yu ;

Lin, Chung-Chang ;

Cheng, Hsin-Mei ;

Liu, Rai-Shung .

ORGANIC LETTERS, 2006, 8 (14) :3153-3156

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