Gold(I)/(III)-catalyzed synthesis of 2-substituted piperidines; valency-controlled cyclization modes

被引：20

作者：

Morita, Nobuyoshi ^{[1
]}

Tsunokake, Tomonori ^{[1
]}

Narikiyo, Yuji ^{[1
]}

Harada, Mayuka ^{[1
]}

Tachibana, Tatsuyuki ^{[1
]}

Saito, Yuta ^{[1
]}

Ban, Shintaro ^{[1
]}

Hashimoto, Yoshimitsu ^{[1
]}

Okamoto, Iwao ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 45期

关键词：

Oxophilic gold(III) catalyst; pi-Philic gold(I) catalyst; Cyclization; Meyer-Schuster rearrangement; Aza-Michael addition; MEYER-SCHUSTER REARRANGEMENT; AZA-MICHAEL REACTION; STEREOSELECTIVE ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PROPARGYLIC ALCOHOLS; ALKALOIDS; (+)-SEDAMINE; GOLD; SEDAMINE; LOBELINE;

D O I：

10.1016/j.tetlet.2015.09.115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strategic use of hard gold(III) and soft gold(I) catalysts provides facile access to two types of 2-substituted piperidines from propargylic alcohols. Thus, heating propargylic alcohols in the presence of AuBr3 results in cyclization to furnish piperidines having an acetylenic moiety, due to activation of the propargylic hydroxyl group by coordination of gold(III). On the other hand, the catalyst [Ph3PAuNTf2](2)PhMe induces Meyer-Schuster rearrangement of propargylic alcohols to give alpha,beta-unsaturated ketones, which undergo intramolecular aza-Michael addition to afford piperidines bearing a carbonyl group, due to activation of the triple bond by coordination of gold(I). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6269 / 6272

页数：4

共 50 条

[31] Gold(I)-Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes
Ikeuchi, Takaya
Inuki, Shinsuke
Oishi, Shinya
Ohno, Hiroaki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (23) : 7792 - 7796
[32] Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles
Benedetti, Erica
Lemiere, Gilles
Chapellet, Laure-Lise
Penoni, Andrea
Palmisano, Giovanni
Malacria, Max
Goddard, Jean-Philippe
Fensterbank, Louis
ORGANIC LETTERS, 2010, 12 (19) : 4396 - 4399
[33] Synthesis and Acid-Catalyzed Cyclization of 2-Alkenylstilbenes: a New Approach to the Substituted Indenes
Ding, Wei
Shi, Xiaoxin
Lu, Xia
CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (11) : 1276 - 1286
[34] Synthesis of substituted β-carbolines via gold(III)-catalyzed cycloisomerization of N-propargylamides
Verniest, Guido
England, Dylan
De Kimpe, Norbert
Padwa, Albert
TETRAHEDRON, 2010, 66 (07) : 1496 - 1502
[35] Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade
Wang, Tao
Shi, Shuai
Rudolph, Matthias
Hashmi, A. Stephen K.
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (10) : 2337 - 2342
[36] Regioselective Mercury(I)/Palladium(II)-Catalyzed Single-Step Approach for the Synthesis of Imines and 2-Substituted Indoles
Gutierrez, Rsuini U.
Hernandez-Montes, Mayra
Mendieta-Moctezuma, Aaron
Delgado, Francisco
Tamariz, Joaquin
MOLECULES, 2021, 26 (13):
[37] Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines
Kumar, Amit
Vachhani, Dipak D.
Modha, Sachin G.
Sharma, Sunil K.
Parmar, Virinder S.
Van der Eycken, Erik V.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2097 - 2102
[38] Proline catalyzed, one-pot three component Mannich reaction and sequential cyclization toward the synthesis of 2-substituted piperidine and pyrrolidine alkaloids
Chacko, Shibin
Ramapanicker, Ramesh
TETRAHEDRON LETTERS, 2015, 56 (15) : 2023 - 2026
[39] Synthesis of 2,5-Substituted Tetrahydrofurans by Pd(II)-Catalyzed Cyclization
Olszewska, Beata
Kryczka, Boguslaw
Zawisza, Anna
LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (08) : 563 - 567
[40] A New Copper(I)-Catalyzed Cycloetherification/Acid-Catalyzed Allylic Nucleophilic Substitution for One-Pot Synthesis of 2-Substituted Benzofurans
Li, Xin
Xue, Jijun
Chen, Rui
Li, Ying
SYNLETT, 2012, (07) : 1043 - 1046

← 1 2 3 4 5 →