PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones

被引：55

作者：

Chang, Hsu-Kai ^{[1
]}

Datta, Swarup ^{[1
]}

Das, Arindam ^{[1
]}

Odedra, Arjan ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 25期

关键词：

alkynes; cyclization; homogeneous catalysis; platinum; spiroketones;

D O I：

10.1002/anie.200700022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Triple rounds: A regioselective hydrative cyclization of triynes has been developed to give bicyclic β-hydroxy spiro ketones, which undergo subsequent dehydration to give the β,γ- unsaturated ketones (see scheme). Model reactions suggest that this platinum catalysis includes two selective hydrations, an alkyne insertion, and an aldol condensation. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4744 / 4747

页数：4

共 29 条

[1] AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].

Asao, N ;

Aikawa, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459

[2] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[3] Hydration of alkynes by a PtCl4-CO catalyst [J].

Baidossi, W ;

Lahav, M ;

Blum, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :669-672

[4] 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

[5] 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

[6] EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST [J].

FUKUDA, Y ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3729-3731

[7] 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

[8] 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

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

Furstner, Alois ;

Aissa, Christophe .

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

[10] CATALYTIC HYDRATION OF ALKYNES WITH ZEISE DIMER [J].

HISCOX, W ;

JENNINGS, PW .

ORGANOMETALLICS, 1990, 9 (07) :1997-1999

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