A highly reactive titanium precatalyst for intramolecular hydroamination reactions

被引:142
作者
Ackermann, L
Bergman, RG [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ol0256724
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Tetrakisamido titanium complexes are significantly more active than Cp2TiMe2 (1) in the intramolecular hydroamination of aminoalkynes and aminoallenes. In the latter case, the regioselectivity of the transformation depends on the nature of the precatalyst, yielding the most selective and reactive catalysis with the bis(sulfonamido) complex 11.
引用
收藏
页码:1475 / 1478
页数:4
相关论文
共 36 条
[1]   The two component palladium catalyst system for intermolecular hydroamination of allenes [J].
AlMasum, M ;
Meguro, M ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1997, 38 (34) :6071-6074
[2]   Intramolecular hydroamination cyclization of aminoallenes catalyzed by organolanthanide complexes. Scope and mechanistic aspects [J].
Arredondo, VM ;
McDonald, FE ;
Marks, TJ .
ORGANOMETALLICS, 1999, 18 (10) :1949-1960
[3]   Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].
Arredondo, VM ;
Tian, S ;
McDonald, FE ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639
[4]   Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoallenes [J].
Arredondo, VM ;
McDonald, FE ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4871-4872
[5]   CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES [J].
ARSENIYADIS, S ;
GORE, J .
TETRAHEDRON LETTERS, 1983, 24 (37) :3997-4000
[6]   VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].
BARANGER, AM ;
WALSH, PJ ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763
[7]  
Bytschkov I, 2001, EUR J ORG CHEM, V2001, P4411
[8]   ASYMMETRIC-SYNTHESIS VIA ELECTROPHILE-MEDIATED CYCLIZATIONS [J].
FOX, DNA ;
GALLAGHER, T .
TETRAHEDRON, 1990, 46 (13-14) :4697-4710
[9]  
Haak E, 1999, ANGEW CHEM INT EDIT, V38, P3389, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3389::AID-ANIE3389>3.0.CO
[10]  
2-E