Reaction of dianions of acyclic beta-enamino ketones with electrophiles .8(a). Synthesis of trialkylsilylenaminones and alpha'-silylated beta-diketones

被引：8

作者：

Bartoli, G

Bosco, M

Dalpozzo, R

DeNino, A

Iantorno, E

Tagarelli, A

Palmieri, G

机构：

[1] DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY

[2] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87030 RENDE,COSENZA,ITALY

[3] DIPARTIMENTO SCI CHIM,I-62032 CAMERINO,MACERATA,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 27期

关键词：

D O I：

10.1016/0040-4020(96)00468-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha'- and gamma-Dianions of beta-(monoalkylamino) alpha,beta-unsaturated ketones react with trialkylchlorosilanes leading to alpha'- and gamma-trialkylsilylenaminones. Conversely from trimethylchlorosilane, the reaction between dianions of 3-(N-isopropylamino)-1-arylbut-2-en-1-ones and t-butyldimethylchlorosilane or triisopropylchlorosilane leads to the corresponding 4-trialkylsilyl derivatives. An explanation of these findings is reported. Hydrolysis of these compounds affords the until now unknown alpha' silylated beta-diketones. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：9179 / 9186

页数：8

相关论文

共 17 条

[1] STEREOSELECTIVE CARBON-CARBON BOND FORMATION - GAMMA-ALKYLATION OF LITHIUM DIANION OF CHIRAL CYCLIC BETA-ENAMINO KETONES [J].

BARTOLI, G ;

CIMARELLI, C ;

PALMIERI, G ;

RAFAIANI, G .

TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :719-722

[2]

Bartoli G, 1996, GAZZ CHIM ITAL, V126, P25

[3] THE REACTION OF THE DIANION OF BETA-ENAMINOKETONES WITH ELECTROPHILES .6. SYNTHESIS OF GAMMA'-NITRO-BETA-ENAMINOKETONE AND EPSILON-NITRO-BETA-ENAMINOKETONE [J].

BARTOLI, G ;

BOSCO, M ;

DALPOZZO, R ;

DENINO, A ;

PALMIERI, G .

TETRAHEDRON, 1994, 50 (32) :9831-9836

[4] REACTION OF DIANION BETA-ENAMINO KETONES WITH ELECTROPHILES .4. SYNTHESIS OF BETA'-HYDROXY-BETA-ENAMINO AND DELTA-HYDROXY-BETA-ENAMINO KETONES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

PALMIERI, G .

TETRAHEDRON, 1993, 49 (12) :2521-2532

[5] REACTION OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES WITH ELECTROPHILES .3. NITRILES - SYNTHESIS OF PYRIDINE AND PYRIMIDINE-DERIVATIVES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

DEMUNNO, G ;

GUERCIO, G ;

PALMIERI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :6020-6025

[6] REACTION OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES WITH ELECTROPHILES .2. OXIRANES - SYNTHESIS OF GAMMA'-HYDROXY-BETA-ENAMINO AND EPSILON-HYDROXY-BETA-ENAMINO KETONES AND OF ALPHA-TETRAHYDROFURYLIDENE KETONES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

PALMIERI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (16) :2095-2100

[7] SELECTIVITY IN C-ALKYLATION OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

GUERRA, M ;

PALMIERI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :649-655

[8] REACTIONS OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES WITH ELECTROPHILES .5. ESTERS - SYNTHESIS OF PYRIDIN-4-ONE AND PYRAN-4-ONE DERIVATIVES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

GUERCIO, G ;

PALMIERI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (17) :2081-2086

[9] STEREOSELECTIVE ALKYLATION OF CYCLIC AND ACYCLIC CHIRAL BETA-ENAMINO KETONES LITHIUM DIANIONS - SYNTHESIS OF EITHER (R)-CHIRAL OR (S)-CHIRAL 1,3-DIKETONES [J].

BARTOLI, G ;

BOSCO, M ;

CIMARELLI, C ;

DALPOZZO, R ;

DEMUNNO, G ;

PALMIERI, G .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1651-1665

[10] UNEXPECTED ELIMINATION TO ALPHA,BETA-ALKYNYLKETONES IN THE REACTION OF DIANIONS OF 1-ARYLENAMINONES WITH TRIMETHYLCHLOROSILANE [J].

BARTOLI, G ;

CIMARELLI, C ;

PALMIERI, G ;

BOSCO, M ;

DALPOZZO, R .

TETRAHEDRON LETTERS, 1991, 32 (48) :7091-7092