Lewis acid mediated [2,3]-sigmatropic rearrangement of allylic ammonium ylides

被引：11

作者：

Blid, J ^{[1
]}

Somfai, P ^{[1
]}

机构：

[1] Royal Inst Technol, Dept Chem Organ Chem, S-10044 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 15期

关键词：

2,3]-sigmatropic rearrangement; ammonium ylide; Lewis acid;

D O I：

10.1016/S0040-4039(03)00510-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation of the Lewis acid mediated [2,3]-sigmatropic rearrangement of allylic ammonium ylides has been conducted by employing various bases and boron Lewis acids. Using BBr3 together with the phosphazene base 6, various allylic amines could be rearranged in good yields with low to excellent diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3159 / 3162

页数：4

共 25 条

[1] [Anonymous], LEWIS ACIDS ORGANIC, DOI DOI 10.1002/9783527618309.CH4
[2] Arboré APA, 2000, SYNLETT, P236
[3] Investigations into the [2,3]-aza-Wittig rearrangement of N-alkyl N-allyl α-amino esters
Coldham, I
Middleton, ML
Taylor, PL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2817 - 2821
[4] REARRANGEMENTS OF YLIDES GENERATED FROM REACTIONS OF DIAZO-COMPOUNDS WITH ALLYL ACETALS AND THIOKETALS BY CATALYTIC METHODS - HETEROATOM ACCELERATION OF THE [2,3]-SIGMATROPIC REARRANGEMENT
DOYLE, MP
GRIFFIN, JH
CHINN, MS
VANLEUSEN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) : 1917 - 1925
[5] HIGHLY EFFECTIVE CATALYTIC METHODS FOR YLIDE GENERATION FROM DIAZO-COMPOUNDS - MECHANISM OF THE RHODIUM-CATALYZED AND COPPER-CATALYZED REACTIONS WITH ALLYLIC COMPOUNDS
DOYLE, MP
TAMBLYN, WH
BAGHERI, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) : 5094 - 5102
[6] Chiral borane-amine adducts in asymmetric synthesis: Alkylation of alanine derivatives
Ferey, V
Toupet, L
LeGall, T
Mioskowski, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04): : 430 - 432
[7] [2,3] SIGMATROPIC REARRANGEMENT OF YLIDES DERIVED FROM BENZYLIC SELENONIUM SALTS
GASSMAN, PG
MIURA, T
MOSSMAN, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) : 954 - 959
[8] Chirality transfer from carbon to nitrogen to carbon via cyclic ammonium ylides
Glaeske, KW
West, FG
[J]. ORGANIC LETTERS, 1999, 1 (01) : 31 - 33
[9] Honda K, 1998, SYNLETT, P685
[10] BASE-CATALYZED REARRANGEMENTS INVOLVING YLIDE INTERMEDIATES .2. THE STEVENS [1,2] AND [3,2] SIGMATROPIC REARRANGEMENTS OF ALLYLIC AMMONIUM YLIDES
JEMISON, RW
LAIRD, T
OLLIS, WD
SUTHERLAND, IO
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07): : 1450 - 1457

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