Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynest

被引:54
作者
Feuvrie, C
Blanchet, J
Bonin, M
Micouin, L
机构
[1] CNRS, UMR 8638, Chim Therapeut Lab, F-75270 Paris 06, France
[2] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
关键词
D O I
10.1021/ol049346v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Terminal alumination of alkynes by DIBALH or trimethylaluminum can be performed in a simple manner in the presence of a small amount of triethylamine. This new Lewis-base-catalyzed process delivers mixed alkynyldialkylalanes of great interest, without the need of an initial deprotonation step with lithium or sodium derivatives followed by a transmetalation.
引用
收藏
页码:2333 / 2336
页数:4
相关论文
共 46 条
[21]   Chiral non-racemic N-cyanomethyloxazolidines:: the pivotal system of the CN(R,S) method [J].
Husson, HP ;
Royer, J .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (06) :383-394
[22]   EFFICIENT LIGANDS, CHIRAL 2-[2,2-DIMETHYL-1-(2-PYRIDYL)PROPOXY]-1,1-DIARYLETHANOLS FOR HIGHLY ENANTIOSELECTIVE ADDITION OF ALKYNYLZINC REAGENTS TO VARIOUS ALDEHYDES [J].
ISHIZAKI, M ;
HOSHINO, O .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1901-1904
[23]   Synthesis of enantiomerically enriched propargylamines by copper-catalyzed addition of alkynes to enamines [J].
Koradin, C ;
Gommermann, N ;
Polborn, K ;
Knochel, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (12) :2797-2811
[24]  
Koradin C, 2002, ANGEW CHEM INT EDIT, V41, P2535, DOI 10.1002/1521-3773(20020715)41:14<2535::AID-ANIE2535>3.0.CO
[25]  
2-M
[26]   Enantioselective alkynylation of aromatic ketones catalyzed by chiral camphorsulfonamide ligands [J].
Lu, G ;
Li, XS ;
Jia, X ;
Chan, WL ;
Chan, ASC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) :5057-5058
[27]   Titanium-catalyzed enantioselective alkynylation of aldehydes [J].
Lu, G ;
Li, XS ;
Chan, WL ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2002, (02) :172-173
[28]   BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes [J].
Moore, D ;
Pu, L .
ORGANIC LETTERS, 2002, 4 (11) :1855-1857
[29]   Palladium-catalyzed alkynylation [J].
Negishi, E ;
Anastasia, L .
CHEMICAL REVIEWS, 2003, 103 (05) :1979-2017
[30]  
NEGISHI EI, 1980, ORGANOMETALLICS MAIN, P286