N-Acyliminium ion cyclisation versus rearrangement.: The synthesis of 13,13-dimethylberberines and 3,4-dimethylisoquinolin-1-ones

被引：16

作者：

Heaney, H ^{[1
]}

Taha, MO ^{[1
]}

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 12期

关键词：

amido-alcohols; cyclisation; diastereoselection; nitrogen heterocycles;

D O I：

10.1016/S0040-4039(00)00081-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective reduction of a range of N-substituted-4,4-dimethylhomophthalimid derivatives gave the related carbinol amides that function as acyliminium ion precursors in the presence of Lewis or protic acids; the fate of the acyliminium ions is determined in part by the nucleophilicity of the beta-arylethyl group on nitrogen, the electrophile used to generate the ion, and the precise reaction conditions and led either to cyclisation reactions or methyl migration. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1993 / 1996

页数：4

共 26 条

[1] A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives
Allin, SM
Northfield, CJ
Page, MI
Slawin, AMZ
[J]. TETRAHEDRON LETTERS, 1999, 40 (01) : 143 - 146
[2] A new approach to the synthesis of non-racemic isoindolin-1-one derivatives
Allin, SM
Northfield, CJ
Page, MI
Slawin, AMZ
[J]. TETRAHEDRON LETTERS, 1999, 40 (01) : 141 - 142
[3] DEPENDENCE OF ARYL ETHER ACYLATION UPON LEWIS ACID STOICHIOMETRY
BUCKLEY, TF
RAPOPORT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) : 3056 - 3062
[4] Enantioselective synthesis of (-)-indolizidine 167B
Chalard, P
Remuson, R
Gelas-Mialhe, Y
Gramain, JC
Canet, I
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1661 - 1664
[5] Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)-lasubine II and (+)-subcosine II
Chalard, P
Remuson, R
Gelas-Mialhe, Y
Gramain, JC
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (24) : 4361 - 4368
[6] Metalation vs nucleophilic addition in the reactions of N-phenethylimides with organolithium reagents. Ready access to isoquinoline derivatives via N-acyliminium ions and Parham-type cyclizations
Collado, MI
Manteca, I
Sotomayor, N
Villa, MJ
Lete, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) : 2080 - 2092
[7] Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine.
Comins, DL
Thakker, PM
Baevsky, MF
Badawi, MM
[J]. TETRAHEDRON, 1997, 53 (48) : 16327 - 16340
[8] Dhimane H, 1998, EUR J ORG CHEM, V1998, P1955
[9] An acyliminium ion approach towards the synthesis of beta-substituted 3,4-dihydroisoquinolone propionates
Fisher, MJ
Gunn, BP
Um, S
Jakubowski, JA
[J]. TETRAHEDRON LETTERS, 1997, 38 (33) : 5747 - 5750
[10] GRODNEY MA, 1999, J ORG CHEM, V64, P556

← 1 2 3 →