First direct C-2-lithiation of 4-DMAP. Convenient access to reactive functional derivatives and ligands

被引:70
作者
Cuperly, D [1 ]
Gros, P [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, Fac Sci, CNRS UHP, UMR 7565, F-54506 Vandoeuvre Les Nancy, France
关键词
D O I
10.1021/jo016064p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first direct alpha-lithiation of 4-DMAP has been peformed via reaction with the BuLi-Me2N(CH2)(2)-OLi (BuLi-LiDMAE) reagent. This new methodology avoids the use of a activation-lithiation-regeneration sequence or halogen-metal exchange classically employed. New useful DMAP-containing synthons and polyheterocycles have been efficiently prepared.
引用
收藏
页码:238 / 241
页数:4
相关论文
共 22 条
[11]   Dialkylchromium complexes bearing a hydrotris(3,5-dimethylpyrazolyl)borate ligand:: synthesis and crystal structures of Tp*CrMe2(DMAP) and Tp*Cr(Cr(CH2Ph)2(DMAP) (DMAP = 4-dimethylaminopyridine) [J].
Mashima, K ;
Oshiki, T ;
Tani, K ;
Aoshima, T ;
Urata, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 569 (1-2) :15-19
[12]   Unprecedented C-6 functionalisation of 3-picoline induced by a methyl to C-6 lithium shift [J].
Mathieu, J ;
Gros, P ;
Fort, Y .
CHEMICAL COMMUNICATIONS, 2000, (11) :951-952
[13]   PYRIDYLPHOSPHINES [J].
NEWKOME, GR .
CHEMICAL REVIEWS, 1993, 93 (06) :2067-2089
[14]   Novel amine chemistry based on DMAP-catalyzed acylation [J].
Ragnarsson, U ;
Grehn, L .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (08) :494-501
[15]   Kinetic resolution of arylalkylcarbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for nonenzymatic acylation [J].
Ruble, JC ;
Tweddell, J ;
Fu, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2794-2795
[16]   Studies on the mechanism of action of 2-formyl-4-pyrrolidinopyridine: Isolation and characterization of a reactive intermediate [J].
Sammakia, T ;
Hurley, TB .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4652-4664
[17]  
Spivey A. C., 2001, J CHEM SOC P1, V15, P1785
[18]   Synthesis of C2-symmetric analogues of 4-(pyrrolidino)pyridine:: new chiral nucleophilic catalysts [J].
Spivey, AC ;
Maddaford, A ;
Fekner, T ;
Redgrave, AJ ;
Frampton, CS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3460-3468
[19]   Preparation and structure of [RhCl(nbd)(dmap)] (nbd = bicyclo[2.2.1]hepta-2,5-diene; dmap = 4-(N,N-dimethylamino)pyridine) [J].
Takenaka, Y ;
Osakada, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (01) :129-130
[20]   Kinetic resolution of secondary alcohols. Enantioselective acylation mediated by a chiral (dimethylamino)pyridine derivative [J].
Vedejs, E ;
Chen, XH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) :1809-1810