Addition of N-Acyliminium Ion Pools to Alkenes Having a Nucleophilic Moiety: Integration of Intermolecular and Intramolecular Reactions

被引：10

作者：

Ashikari, Yosuke ^{[1
]}

Kiuchi, Yohei ^{[1
]}

Takeuchi, Tomoya ^{[1
]}

Ueoka, Koji ^{[1
]}

Suga, Seiji ^{[1
]}

Yoshida, Jun-ichi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

CHEMISTRY LETTERS | 2014年 / 43卷 / 02期

关键词：

PD-CATALYZED CARBOETHERIFICATION; ASYMMETRIC-SYNTHESIS; CHEMICAL OXIDATION; COUPLING REACTIONS; ANODIC-OXIDATION; IN-SITU; CYCLOADDITION; GENERATION; HETEROCYCLES; CYCLIZATIONS;

D O I：

10.1246/cl.130947

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of electrochemically generated N-acyliminium ion pools with alkenes bearing a heteroatom nucleophilic functionality such as a hydroxy group, a carboxy group, and an oxime moiety led to intermolecular carbon carbon bond formation followed by intramolecular carbon heteroatom bond formation to give the corresponding heterocyclic compounds such as cyclic ethers, lactones, and 2-isoxazolines, respectively.

引用

页码：210 / 212

页数：3

共 50 条

[31] Scope and limitations of the solution and solid phase synthesis of homoallylic amines via N-acyliminium ion reactions
Meester, WJN
van Maarseveen, JH
Kirchsteiger, K
Hermkens, PHH
Schoemaker, HE
Hiemstra, H
Rutjes, FPJT
ARKIVOC, 2004, : 122 - 151
[32] TOTAL SYNTHESIS OF (+/-)-ALPHA-ALLOKAINIC ACID VIA 2 ALLYLSILANE N-ACYLIMINIUM ION REACTIONS
MOOIWEER, HH
HIEMSTRA, H
SPECKAMP, WN
TETRAHEDRON, 1991, 47 (20-21) : 3451 - 3462
[33] On-bead MALDI-MS monitoring of solid-supported N-acyliminium ion reactions
Nachtigall, F. M.
Santos, L. S.
JOURNAL OF MASS SPECTROMETRY, 2017, 52 (04): : 254 - 258
[34] A novel acid stable/base labile carbamate linker for N-acyliminium ion reactions on solid support
Veerman, JJN
Rutjes, FPJT
van Maarseveen, JH
Hiemstra, H
TETRAHEDRON LETTERS, 1999, 40 (33) : 6079 - 6082
[35] Mannich-type reactions in the gas-phase:: The addition of enol silanes to cyclic N-acyliminium ions
Tomazela, DM
Moraes, LAB
Pilli, RA
Eberlin, MN
D'Oca, MGM
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4652 - 4658
[36] 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
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07): : 2080 - 2092
[37] Tandem Diels-Alder N-Acyliminium Ion Cyclization Reactions. A New Entry into the Erythrinane Skeleton
J Org Chem, 15 (4888):
[38] Tandem Diels-Alder N-acyliminium ion cyclization reactions. A new entry into the erythrinane skeleton
Padwa, A
Kappe, CO
Reger, TS
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15): : 4888 - 4889
[39] 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
[40] Toward improving the chemistry of N-acyliminium ions:: Nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)
Ben Othman, R
Bousquet, T
Fousse, A
Othman, M
Dalla, V
ORGANIC LETTERS, 2005, 7 (14) : 2825 - 2828

← 1 2 3 4 5 →