NOVEL SYNTHESIS OF HETEROCYCLES USING ZIRCONIUM-CATALYZED DIENE CYCLIZATION

被引：38

作者：

UESAKA, N

MORI, M

OKAMURA, K

DATE, T

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO 060,JAPAN

[2] TANABE SEIYAKU CO LTD,CTR ANALYT,TODA,SAITAMA 335,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic cyclization of the diene 1 by Cp(2)ZrCl(2) in the presence of BuMgBr gives the hexahydroindole derivative 2. The stereochemistry of the zirconacycle 10 is different from that of the zirconacycle 7, which is obtained from 1 under stoichiometric conditions. Carbon-carbon bond formation results from treatment of the intermediary magnesium complex 8 with various electrophiles, such that various heterocycles were synthesized.

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页码：4542 / 4547

页数：6

相关论文

共 25 条

[1] GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058

[2] SYNTHESIS, STRUCTURE, AND REACTIONS OF A ZIRCONOCENE CYCLOHEXYNE COMPLEX [J].

BUCHWALD, SL ;

LUM, RT ;

DEWAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7441-7442

[3] THE TRIMETHYLPHOSPHINE ADDUCT OF THE ZIRCONOCENE BENZYNE COMPLEX - SYNTHESIS, REACTIONS, AND X-RAY CRYSTAL-STRUCTURE [J].

BUCHWALD, SL ;

WATSON, BT ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7411-7413

[4] SOME NOVELTIES IN OLEFIN CARBOMETALLATION ASSISTED BY ALKYL-MAGNESIUM AND ALKYL-ALUMINUM DERIVATIVES AND CATALYZED BY ZIRCONIUM AND TITANIUM COMPLEXES [J].

DZHEMILEV, UM ;

VOSTRIKOVA, OS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :43-51

[5] HOMOGENEOUS ZIRCONIUM BASED CATALYSTS IN ORGANIC-SYNTHESIS [J].

DZHEMILEV, UM ;

VOSTRIKOVA, OS ;

TOLSTIKOV, GA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 304 (1-2) :17-39

[6] ZIRCONIUM-CATALYZED ETHYLMAGNESATION OF HYDROXYLATED TERMINAL ALKENES - A CATALYTIC AND DIASTEREOSELECTIVE CARBON-CARBON BOND-FORMING REACTION [J].

HOURI, AF ;

DIDIUK, MT ;

XU, ZM ;

HORAN, NR ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6614-6624

[7] STEREOSELECTIVE FORMATION OF CARBON CARBON BONDS THROUGH METAL CATALYSIS - THE ZIRCONIUM-CATALYZED ETHYLMAGNESATION REACTION [J].

HOVEYDA, AH ;

XU, ZM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5079-5080

[8] STEREOSELECTIVE ZIRCONIUM-CATALYZED ETHYLMAGNESATION OF HOMOALLYLIC ALCOHOLS AND ETHERS - THE INFLUENCE OF INTERNAL LEWIS-BASES ON SUBSTRATE REACTIVITY [J].

HOVEYDA, AH ;

XU, ZM ;

MORKEN, JP ;

HOURI, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8950-8952

[9] REGIOSELECTIVE AND STEREOSELECTIVE CARBON-CARBON BOND FORMATION THROUGH TRANSITION-METAL CATALYSIS - THE INFLUENCE OF CATALYST CHIRALITY ON SELECTIVE ETHYLMAGNESATION OF CHIRAL, NONRACEMIC ALCOHOLS AND ETHERS [J].

HOVEYDA, AH ;

MORKEN, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4237-4244

[10] ON THE MECHANISM OF THE ZIRCONIUM-CATALYZED CARBOMAGNESATION REACTION - EFFICIENT AND SELECTIVE CATALYTIC CARBOMAGNESATION WITH HIGHER ALKYLS OF MAGNESIUM [J].

HOVEYDA, AH ;

MORKEN, JP ;

HOURI, AF ;

XU, ZM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6692-6697