DOUBLE (INTERNAL EXTERNAL) ALKYNE INSERTION REACTIONS OF ALPHA-DIAZOKETONES

被引：40

作者：

HOYE, TR

DINSMORE, CJ

机构：

[1] Department of Chemistry University of Minnesota, Minneapolis

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

INTRAMOLECULAR ADDITION; DIAZO KETONES;

D O I：

10.1016/S0040-4039(00)79368-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetylenic alpha-diazoketone 5, when treated with Rh2(OAc)4 and several different alkynes, gives alkyne insertion/cyclopropenation products. Subsequent catalytic ring opening reactions demonstrate a highly regioselective net double alkyne insertion process and a new dihydropentalenone synthesis.

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页码：3755 / 3758

页数：4

相关论文

共 7 条

[1] A NEW, GENERAL CYCLOPENTENONE SYNTHESIS [J].

CECCHERELLI, P ;

CURINI, M ;

MARCOTULLIO, MC ;

ROSATI, O ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :311-315

[2] ALKYNE INSERTION REACTIONS OF METAL-CARBENES DERIVED FROM ENYNYL ALPHA-DIAZO KETONES [R'CN2COCR2CH2C=C(CH2)N-2CH=CH2] [J].

HOYE, TR ;

DINSMORE, CJ ;

JOHNSON, DS ;

KORKOWSKI, PF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4518-4520

[3]

HOYE TR, IN PRESS J AM CHEM S

[4] RH(II)-CATALYZED ISOMERIZATIONS OF CYCLOPROPENES - EVIDENCE FOR RH(II)-COMPLEXED VINYLCARBENE INTERMEDIATES [J].

MULLER, P ;

PAUTEX, N ;

DOYLE, MP ;

BAGHERI, V .

HELVETICA CHIMICA ACTA, 1990, 73 (05) :1233-1241

[5] CYCLOALKENONE FORMATION BY THE INTRAMOLECULAR ADDITION OF A ALPHA-DIAZOKETONE TO AN ACETYLENIC PI-BOND [J].

PADWA, A ;

KRUMPE, KE ;

ZHI, L .

TETRAHEDRON LETTERS, 1989, 30 (20) :2633-2636

[6] RHODIUM(II)-CATALYZED CYCLIZATION REACTIONS OF ALKYNYL-SUBSTITUTED ALPHA-DIAZO KETONES [J].

PADWA, A ;

KRUMPE, KE ;

GAREAU, Y ;

CHIACCHIO, U .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2523-2530

[7] GENERATION OF VINYLCARBENES BY THE INTRAMOLECULAR ADDITION OF ALPHA-DIAZO KETONES TO ACETYLENES [J].

PADWA, A ;

CHIACCHIO, U ;

GARREAU, Y ;

KASSIR, JM ;

KRUMPE, KE ;

SCHOFFSTALL, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :414-416