Synthetic utility of organometallic reagents derived from group IV metal tetrachlorides and CH3Li.: A direct synthesis of 2-(2-keto-1-alkylidene)tetrahydropyrroles from 4-alkynylamines and acyl cyanides

被引:24
作者
Duncan, D [1 ]
Livinghouse, T [1 ]
机构
[1] Montana State Univ, Dept Chem, Bozeman, MT 59717 USA
关键词
D O I
10.1021/om9902380
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The non-Cp-bearing titanium alkyls (CH3)(2)TiCl2. L-2 (1a) and (CH3)(2)Ti(OTFE)Cl . L-2 (1b) and their Zr(IV) analogues have been shown to mediate efficient aminoalkyne cyclizations to provide azatitanium intermediates that undergo facial C-acylation in the presence of acyl cyanides.
引用
收藏
页码:4421 / 4428
页数:8
相关论文
共 15 条
[1]   ORGANO-METALLIC TITANIUM COMPOUNDS AS POLYMERIZATION CATALYSTS [J].
BEERMANN, C ;
BESTIAN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1959, 71 (19) :618-623
[2]  
DEBUTTS EH, 1962, Patent No. 3021349
[3]   Scope of the intramolecular imidotitanium-alkyne [2+2] cycloaddition azatitanetine acylation sequence. An efficient procedure for the synthesis of 2-(2-keto-1-alkylidene)tetrahydropyrrole and related compounds [J].
Fairfax, D ;
Stein, M ;
Livinghouse, T ;
Jensen, M .
ORGANOMETALLICS, 1997, 16 (08) :1523-1525
[4]   Preparation of new zirconium benzamidinates: alkyl derivatives and low-valent chemistry yielding metallacycles via coupling of alkynes and ethylene [J].
Hagadorn, JR ;
Arnold, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (18) :3087-3096
[5]   ACYLNITRILIUM ION INITIATED HETEROANNULATIONS IN ALKALOID SYNTHESIS - AN EFFICIENT, STEREOCONTROLLED, TOTAL SYNTHESIS OF THE ORCHIDACEAE ALKALOID (+/-)-DENDROBINE [J].
LEE, CH ;
WESTLING, M ;
LIVINGHOUSE, T ;
WILLIAMS, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4089-4095
[6]   Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes [J].
Li, YW ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9295-9306
[7]   SYNTHETIC APPLICATIONS OF GROUP-IV METAL IMIDO COMPLEX-ALKYNE [2+2] CYCLOADDITIONS - A CONCISE TOTAL SYNTHESIS OF (+/-)-MONOMORINE [J].
MCGRANE, PL ;
LIVINGHOUSE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1323-1324
[8]   INTRAMOLECULAR [2+2] CYCLOADDITIONS OF GROUP-IV METAL IMIDO COMPLEXES - APPLICATIONS TO THE SYNTHESIS OF DIHYDROPYRROLE AND TETRAHYDROPYRIDINE DERIVATIVES [J].
MCGRANE, PL ;
JENSEN, M ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5459-5460
[9]   SYNTHETIC APPLICATIONS OF IMIDOTITANIUM ALKYNE [2+2] CYCLOADDITIONS - A CONCISE, STEREOCONTROLLED TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN [J].
MCGRANE, PL ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11485-11489
[10]   Preparation and structural characterization of an enantiomerically pure, C-2-symmetric, single-component Ziegler-Natta alpha-olefin polymerization catalyst [J].
Mitchell, JP ;
Hajela, S ;
Brookhart, SK ;
Hardcastle, KI ;
Henling, LM ;
Bercaw, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1045-1053