One-Carbon Homologation of α,β-Unsaturated Aldehydes: Access to α-Tertiary β,γ-Unsaturated Aldehydes

被引：2

作者：

Delbrassinne, Arnaud ^{[1
]}

Mba, Boris Junior Takam ^{[1
]}

Collard, Laurent ^{[1
]}

Robiette, Raphael ^{[1
]}

机构：

[1] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, Pl Louis Pasteur 1 Box L4-01-02, B-1348 Louvain La Neuve, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 40期

关键词：

Epoxide; Homologation; Meinwald; Migration; Rearrangement; MEDIATED ASYMMETRIC EPOXIDATIONS; SELECTIVE HYDROFORMYLATION; REARRANGEMENT; EPOXIDES; OXIDATION;

D O I：

10.1002/ejoc.202300765

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol for the synthesis of enolizable alpha-substituted beta,gamma-unsaturated aldehydes is reported. The developed strategy involves two steps, epoxidation and Meinwald rearrangement, to result in a one-carbon homologation of alpha,beta-unsaturated aldehydes enabling the insertion of a CHR unit.

引用

页数：5

共 50 条

[41] Clean and efficient oxidation of homoallylic and homopropargylic alcohols into β,γ-unsaturated aldehydes by the Dess-Martin periodinane
Wavrin, L
Viala, J
SYNTHESIS-STUTTGART, 2002, (03): : 326 - 330
[42] Derailed Ohira-Bestmann Reaction of γ,δ-Unsaturated Aldehydes for the Stereoselective Synthesis of Cyclopenta[c]pyrazoles
Sandmeier, Tobias
Sievertsen, Niels
Carreira, Erick M.
HELVETICA CHIMICA ACTA, 2020, 103 (06)
[43] Copper(I)-Catalyzed Stereoselective Synthesis of (E)-α-Alkynyl-α,β-unsaturated Esters from a Terminal Alkyne, Diazoesters and Aldehydes
Wu, Chenggui
Liu, Zhenxing
Zhang, Zhikun
Ye, Fei
Deng, Guisheng
Zhang, Yan
Wang, Jianbo
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2480 - 2488
[44] A facile synthesis of in-situ formed amorphous zirconia catalysts for efficient transfer hydrogenation of unsaturated aldehydes
Cui, Haishuai
Zhong, Linhao
Lv, Yang
Hao, Fang
Liu, Pingle
Xiong, Wei
Xiong, Shaofeng
Liu, Huajie
Luo, He'an
FUEL, 2022, 317
[45] Confining of PtCo into MCM-41-C for selective hydrogenation of biomass-derived unsaturated aldehydes
Wang, Changlong
Zhao, Ziyi
Peng, Yujie
Ma, Liyao
Liu, Xiang
Fu, Fangyu
Wu, Yufeng
FUEL, 2024, 372
[46] Development and Scale-up of Continuous Electrocatalytic Hydrogenation of Functionalized Nitro Arenes, Nitriles, and Unsaturated Aldehydes
Egbert, Jonathan D.
Thomsen, Edwin C.
O'Neill-Slawecki, Stacy A.
Mans, Douglas M.
Leitch, David C.
Edwards, Lee J.
Wade, Charles E.
Weber, Robert S.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (09) : 1803 - 1812
[47] Synthesis of Tetrasubstituted α, β-Unsaturated Aldehydes via Radical 1,4-Aryl Migration/Trifluoromethylthiolation Cascade Reaction of Aryl Propynyl Ethers
Guo, Chun-Huan
Chen, Dao-Qian
Chen, Si
Liu, Xue-Yuan
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) : 2901 - 2906
[48] TiCl4--mediated olefination of aldehydes with acetic acid and alkyl acetates: a stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters
Augustine, John Kallikat
Boodappa, Chandrakantha
Venkatachaliah, Srinivasa
Mariappan, Ayyampillai
TETRAHEDRON LETTERS, 2014, 55 (24) : 3503 - 3506
[49] Practical Synthesis of Linear α-Iodo/Bromo-α,β-unsaturated Aldehydes/Ketones from Propargylic Alcohols via Au/Mo Bimetallic Catalysis
Ye, Longwu
Zhang, Liming
ORGANIC LETTERS, 2009, 11 (16) : 3646 - 3649
[50] Oxidative Lipidomics to Unravel the Glycerol Core Aldehydes of Three Typical Unsaturated Triglycerides under Simulated Heating Conditions
Liang, Xin
Huang, Luelue
Liu, Ran
Li, Xu
Huang, Xiaoyu
Zhang, Hui
Wang, Xingguo
Wu, Gangcheng
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (51) : 28425 - 28438

← 1 2 3 4 5 →