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
[1]   A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates [J].
Ahn, JH ;
Joung, MJ ;
Yoon, NM ;
Oniciu, DC ;
Katritzky, AR .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :488-492
[2]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[3]  
BINGER P, 1963, ANGEW CHEM INT EDIT, V2, P686
[4]  
Blanchet A, 2002, EUR J ORG CHEM, V2002, P2598
[5]   Asymmetric synthesis of α-substituted propynyl amines.: Application to the preparation of a polysubstituted dihydroisoindoline framework [J].
Blanchet, J ;
Bonin, M ;
Micouin, L ;
Husson, HP .
TETRAHEDRON LETTERS, 2001, 42 (18) :3171-3173
[6]   [2,3]-Meisenheimer rearrangement of N-allyl phenylglycinol derivatives.: N-C versus C-C chirality transfer [J].
Blanchet, J ;
Bonin, M ;
Micouin, L ;
Husson, HP .
TETRAHEDRON LETTERS, 2000, 41 (43) :8279-8283
[7]   Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds [J].
Blanchet, J ;
Bonin, M ;
Chiaroni, A ;
Micouin, L ;
Riche, C ;
Husson, HP .
TETRAHEDRON LETTERS, 1999, 40 (15) :2935-2938
[8]   Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines [J].
Blanchet, J ;
Bonin, M ;
Micouin, L ;
Husson, HP .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6423-6426
[9]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[10]   HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].
COREY, EJ ;
CIMPRICH, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152