Diastereoselective addition of metalated isoindolin-1-ones to aldehydes.: Stereoselective preparation of (E)-3-arylideneisoindolin-1-ones

被引:43
作者
Couture, A [1 ]
Deniau, E [1 ]
Grandclaudon, P [1 ]
Hoarau, C [1 ]
Rys, W [1 ]
机构
[1] Univ Sci & Tech Lille Flandres Artois, Chim Organ Phys Lab, UPRESA 8009, F-59655 Villeneuve Dascq, France
关键词
D O I
10.1016/S0040-4039(02)00236-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithiated isoindolinones react with aromatic aldehydes to afford 3-hydroxybenzyl derivatives with high diastereoselectivity. Dehydration of erythro and threo adducts through an E1cb mechanism gives rise indiscriminately to the (E)-arylideneisoindolinones. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2207 / 2210
页数:4
相关论文
共 17 条
[1]   A facile and highly stereoselective approach to a polycyclic isoindolinone ring system via an N-acyliminium ion cyclization reaction [J].
Allin, SM ;
Northfield, CJ ;
Page, MI ;
Slawin, AMZ .
TETRAHEDRON LETTERS, 1998, 39 (27) :4905-4908
[2]  
Chang Z.-L., 1978, The Alkaloids, V31, P29
[3]   LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives [J].
Couture, A ;
Deniau, E ;
Ionescu, D ;
Grandclaudon, P .
TETRAHEDRON LETTERS, 1998, 39 (16) :2319-2320
[4]   Total syntheses of taliscanine, velutinam, and enterocarpam II [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Hoarau, C .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3128-3132
[5]   An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and Horner reaction of o- (and m-)halogeno-N-phosphorylmethylbenzamide derivatives. [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P .
TETRAHEDRON, 1997, 53 (30) :10313-10330
[6]  
ElGihani MT, 1996, SYNLETT, P871
[7]   A concise total synthesis of the azaphenanthrene alkaloid eupolauramine [J].
Hoarau, C ;
Couture, A ;
Cornet, H ;
Deniau, E ;
Grandclaudon, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8064-8069
[8]   Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates:: a model study for the Tacaman alkaloid D/E ring fusion [J].
Hunter, R ;
Richards, P .
TETRAHEDRON LETTERS, 2000, 41 (19) :3755-3758
[9]  
KATO Y, 1993, CHEM PHARM BULL, V41, P2003
[10]   LEWIS ACID COMPLEXED HETEROATOM CARBANIONS - A CONVENIENT ROUTE TO ALPHA-HYDROXYBENZYLTETRAHYDROISOQUINOLINE ALKALOIDS [J].
KESSAR, SV ;
VOHRA, R ;
KAUR, NP .
TETRAHEDRON LETTERS, 1991, 32 (27) :3221-3224