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
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 51期
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 50 条
  • [31] Asymmetric Bronsted Acid Catalyzed Nucleophilic Addition to in situ Generated Chiral N-Acyliminium Ions
    Rueping, Magnus
    Nachtsheim, Boris J.
    SYNLETT, 2010, (01) : 119 - 122
  • [32] Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
    Grossmann, Oleg
    Maji, Rajat
    Aukland, Miles H.
    Lee, Sunggi
    List, Benjamin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (09)
  • [33] Addition of Carbon-Based Nucleophiles to Fmoc-Protected Acyl Iminium Ions
    Hartman, Alison E.
    Brophy, Cheryl L.
    Cupp, Julia A.
    Hodge, Daniel K.
    Peelen, Timothy J.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3952 - 3954
  • [34] Stereoselective syntheses of (+)-isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium (IV) enolates to cyclic N-acyliminium ions
    Pereira, Elaine
    Alves, Conceicao de Fatima
    Boeckelmann, Maria Alice
    Pilli, Ronaldo A.
    QUIMICA NOVA, 2008, 31 (04): : 771 - 775
  • [35] Synthesis of potassium and tetra n-butylammonium 2-substituted-1,3-dithianotrifluoroborate salts and addition to chiral cyclic N-acyliminium ions
    Vieira, Adriano S.
    Fiorante, Pedro F.
    Zukerman-Schpector, Julio
    Alves, Diego
    Botteselle, Giancarlo V.
    Stefani, Helio A.
    TETRAHEDRON, 2008, 64 (30-31) : 7234 - 7241
  • [36] Generation of N-acyliminium ions via intramolecular conjugate addition reactions:: A strategy for the total synthesis of nakadomarin A
    Nilson, Mark G.
    Funk, Raymond L.
    ORGANIC LETTERS, 2006, 8 (17) : 3833 - 3836
  • [37] Highly stereoselective trans addition of π-type nucleophiles to a bicyclic N-acyliminium ion -: Application to the synthesis of indolizidine and pyrrolizidine alkaloids
    Dhimane, H
    Vanucci-Bacque, C
    Hamon, L
    Lhommet, G
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (09) : 1955 - 1963
  • [38] Stereoselective synthesis of trans-2,3-disubstituted pyrrolidines via addition to N-acyliminium ions
    Buezo, ND
    Jiménez, A
    Pedregal, C
    Vidal, P
    TETRAHEDRON LETTERS, 2006, 47 (15) : 2489 - 2492
  • [39] Diastereoselection of the addition of silyloxyfurans to five-, six- and seven-membered N-acyliminium ions
    de Oliveira, MDF
    Santos, LS
    Pilli, RA
    TETRAHEDRON LETTERS, 2001, 42 (40) : 6995 - 6997
  • [40] Enhanced trans diastereoselection in the allylation of cyclic chiral N-acyliminium ions.: Synthesis of hydroxylated indolizidines
    Klitzke, CF
    Pilli, RA
    TETRAHEDRON LETTERS, 2001, 42 (33) : 5605 - 5608
12345