Triquinanes from linear ketones via trimethylenemethane diyls

被引：17

作者：

Lee, Hee-Yoon ^{[1
]}

Kim, Won-Yeob

Lee, Sejin

机构：

[1] Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Sch Mol Sci BK21, Taejon 305701, South Korea

[2] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 08期

关键词：

alkylidene carbene; trimethylenemethane; diyl; triquinane;

D O I：

10.1016/j.tetlet.2006.12.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Linear compounds containing a ketone and diene functional groups reacted with the anion of TMS-diazomethane to produce alkylidene carbenes that underwent intramolecular cyclopropanation followed by the formation of trimethylenemethane diyls which underwent [2+3] cycloaddition reaction to produce linearly fused triquinanes. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：1407 / 1410

页数：4

相关论文

共 13 条

[1] A RANKING OF DIYLOPHILIC REACTIVITIES OF OLEFINS TOWARD THE SINGLET AND TRIPLET FORMS OF THE TRIMETHYLENEMETHANE BIRADICAL, "2-ISOPROPYLIDENECYCLOPENTA-1,3-DIYL [J].

DUNCAN, CD ;

CORWIN, LR ;

DAVIS, JH ;

BERSON, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (07) :2350-2358

[2] On the absence of stereoselectivity in the catalytic oxidation of alkenes with a surface-bound metalloporphyrin-peptide conjugate [J].

Geier, GR ;

Lybrand, TP ;

Sasaki, T .

TETRAHEDRON, 1999, 55 (07) :1871-1880

[3] GENERATION OF ALKYLIDENE CARBENES FROM ALPHA,BETA-EPOXY-N-AZIRIDINYL IMINES - A NEW ROUTE TO CYCLOPENTENOLS [J].

KIM, S ;

CHO, CM .

TETRAHEDRON LETTERS, 1994, 35 (45) :8405-8408

[4] Alkenylidenes in organic synthesis [J].

Kirmse, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11) :1164-1170

[5] Triquinanes from linear alkylidene carbenes via trimethylenemethane diyls [J].

Lee, HY ;

Kim, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10156-10157

[6] INTRAMOLECULAR DIYL TRAPPING - TOTAL SYNTHESIS OF DL-HIRSUTENE [J].

LITTLE, RD ;

MULLER, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2744-2749

[7]

Little RD., 2000, STUDIES NATURAL PROD, V22, P195

[8] ABSOLUTE RATES OF TRIPLET-TRIPLET DIMERIZATION AND CYCLOADDITION OF TRIMETHYLENEMETHANE BIRADICALS [J].

PLATZ, MS ;

BERSON, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6743-6744

[9] SOME REACTIONS OF DIMETHYLPHOSPHONO-SUBSTITUTED DIAZOALKANES - (MEO)2P(O)CR TRANSFER TO OLEFINS AND 1,3-DIPOLAR ADDITIONS OF (MEO)2P(O)C(N2)R [J].

SEYFERTH, D ;

MARMOR, RS ;

HILBERT, P .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (10) :1379-&

[10] Trimethylsilyldiazomethane: A useful reagent for generating alkylidene carbenes and its application to organic synthesis [J].

Shioiri, T ;

Aoyama, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (11) :918-928