Addition of silylated carbon nucleophiles to iminium and cyclic N-acyliminium ions promoted by InCl3

被引:42
作者
Russowsky, D [1 ]
Petersen, RZ
Godoi, MN
Pilli, RA
机构
[1] Univ Fed Rio Grande do Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil
[2] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil
关键词
D O I
10.1016/S0040-4039(00)01828-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
InCl3 was used as Lewis acid in the addition of silyl enolates and allyltrimethylsilane to aromatic aldimines and cyclic N-acyliminium ions derived from 5-acetoxylactams affording beta -aminocarbonyl systems and allyl adducts, respectively, in reasonable to good yields. The diastereofacial selectivity of cyclic N-acyliminium ions was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9939 / 9942
页数:4
相关论文
共 14 条
[1]  
[Anonymous], [No title captured]
[2]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[3]  
2-E
[4]   Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex [J].
Fujii, A ;
Hagiwara, E ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5450-5458
[5]  
HISHITANI H, 1997, J AM CHEM SOC, V119, P7153
[6]   Three component synthesis of β-amino carbonyl compounds using indium trichloride-catalyzed one-pot Mannich-type reaction in water [J].
Loh, TP ;
Liung, SBKW ;
Tan, KL ;
Wei, LL .
TETRAHEDRON, 2000, 56 (20) :3227-3237
[7]   Novel one-pot mannich-type reaction in water:: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters [J].
Loh, TP ;
Wei, LL .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :323-326
[8]   Addition of a chiral boron enolate to cyclic N-acyliminium ions. Stereocontrolled synthesis of the pyrrolizidine ring system [J].
Pilli, RA ;
Russowsky, D .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3187-3190
[9]  
Pilli RA, 1997, TREND ORGAN CHEM, V6, P101
[10]   ONE-POT PREPARATION OF QUINOLIZIDIN-2-ONE AND INDOLIZIDIN-7-ONE RING-SYSTEMS - CONCISE TOTAL SYNTHESES OF (+/-)-MYRTINE,(+/-)-LASUBINE-II, AND (-)-INDOLIZIDINE 223AB [J].
PILLI, RA ;
DIAS, LC ;
MALDANER, AO .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :717-722