Silylcyclocarbonylation (SiCCa) of alkynylamines catalyzed by rhodium complexes

被引：10

作者：

Ojima, I

Machnik, D

Donovan, RJ

Mneimne, O

机构：

来源：

INORGANICA CHIMICA ACTA | 1996年 / 251卷 / 1-2期

关键词：

silylcyclocarbonylation; alkynylamines; rhodium-catalyzed; izidine alkaloid;

D O I：

10.1016/S0020-1693(97)82717-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Attempted silylcarbocyclization (SiCaC) of 2-allyl-1-propargyltetrahydroisoquinoline with HSiMe(2)Ph and carbon monoxide catalyzed by Rh(acac)(CO)(2) unexpectedly gives 8-exo-silylmethylene-4, 5-benzo-9-indolizidinone, 8-allyl-8-silylmethyl-4, 5-benzo-9-indolizidinone and a hydrosilylation product. Possible mechanisms are proposed for the observed facile N-allyl cleavage and allyl transfer as well as the silylcyclocarbonylation (SiCCa) of the alkynylamine generated in situ. The SiCCa reactions of 1-propargyltetrahydroisoquinoline, (R)-2-(3-butynyl)pyrrolidine, (S)-2-[(R)-1-hydroxy-3-butynyl]pyrrolidine and (S)-2-[diethynyl-(hydroxy)methyl]pyrrolidine are furthur investigated These reactions give the corresponding indolizidine or pyrrolizidine skeletons in one step. The scope and limitation of the SiCCa reaction and related reactions are discussed.

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页码：299 / 307

页数：9

相关论文

共 29 条

[1] HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SILYLFORMYLATION OF ALKYNES UNDER MILD CONDITIONS PROMOTED BY DIRHODIUM(II) PERFLUOROBUTYRATE [J].

DOYLE, MP ;

SHANKLIN, MS .

ORGANOMETALLICS, 1994, 13 (04) :1081-1088

[2] HIGHLY EFFICIENT REGIOSELECTIVE SILYLCARBONYLATION OF ALKYNES CATALYZED BY DIRHODIUM(II) PERFLUOROBUTYRATE [J].

DOYLE, MP ;

SHANKLIN, MS .

ORGANOMETALLICS, 1993, 12 (01) :11-12

[3] AUXILIARY SILICON IN REGIOSELECTIVE COBALT CATALYZED PROTOBERBERINE SYNTHESES [J].

HILLARD, RL ;

PARNELL, CA ;

VOLLHARDT, KPC .

TETRAHEDRON, 1983, 39 (06) :905-911

[4] COBALT-RHODIUM HEPTACARBONYL - A COORDINATIVELY UNSATURATED DINUCLEAR METAL-CARBONYL [J].

HORVATH, IT ;

BOR, G ;

GARLAND, M ;

PINO, P .

ORGANOMETALLICS, 1986, 5 (07) :1441-1445

[5] DICOBALTOCTACARBONYL-MEDIATED CYCLIZATIONS OF ELECTRON-DEFICIENT ALKYNONES [J].

HOYE, TR ;

SURIANO, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1659-1660

[6] PAUSON-KHAND REACTION WITH ELECTRON-DEFICIENT ALKYNES [J].

KRAFFT, ME ;

ROMERO, RH ;

SCOTT, IL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5277-5278

[7] EFFECT OF COORDINATING LIGANDS ON THE PAUSON-KHAND CYCLOADDITION - TRAPPING OF AN INTERMEDIATE [J].

KRAFFT, ME ;

SCOTT, IL ;

ROMERO, RH ;

FEIBELMANN, S ;

VANPELT, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7199-7207

[8] DICOBALTOCTACARBONYL ALKYNE COMPLEXES AS INTERMEDIATES IN THE SYNTHESIS OF BICYCLO[3.3.0]OCTENONES FOR THE SYNTHESIS OF CORIOLIN AND HIRSUTIC ACID [J].

MAGNUS, P ;

EXON, C ;

ALBAUGHROBERTSON, P .

TETRAHEDRON, 1985, 41 (24) :5861-5869

[9] NEW MIXED TETRANUCLEAR METAL-CARBONYLS OF GROUP-VIIIB [J].

MARTINENGO, S ;

CHINI, P ;

ALBANO, VG ;

CARIATI, F ;

SALVATOR.T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 59 (OCT1) :379-394

[10] READY ACCESS TO ALPHA-(TRIORGANOSILYL)METHYLENE BETA-LACTONES BY MEANS OF RHODIUM-CATALYZED CYCLOCARBONYLATION OF SUBSTITUTED PROPARGYL ALCOHOLS [J].

MATSUDA, I ;

OGISO, A ;

SATO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6120-6121