Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements

被引：28

作者：

Gille, Annika ^{[1
]}

Rehbein, Julia ^{[1
]}

Hiersemann, Martin ^{[1
]}

机构：

[1] Tech Univ Dortmund, Fak Chem, D-44227 Dortmund, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 08期

关键词：

DENSITY-FUNCTIONAL THERMOCHEMISTRY; GOLD(I)-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SOLVENTS;

D O I：

10.1021/ol200558j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed gamma-allenyl alpha-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.

引用

页码：2122 / 2125

页数：4

共 50 条

[31] THERMAL AND CATALYTIC CLAISEN REARRANGEMENT OF PROPARGYL ETHERS OF ISOMERIC ACETYLNAPHTHOLS AND 4,6-DIACETYLRESORCINOL
ANJANEYULU, ASR
ISAA, BM
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1991, 30 (09): : 828 - 833
[32] CLAISEN REARRANGEMENT OF ARYL PROPARGYL ETHERS IN POLY(ETHYLENE GLYCOL) - A REMARKABLE SUBSTITUENT AND SOLVENT EFFECT
RAO, U
BALASUBRAMANIAN, KK
TETRAHEDRON LETTERS, 1983, 24 (45) : 5023 - 5024
[33] Claisen rearrangement of aliphatic allyl vinyl ethers in the presence of copper(II) bisoxazoline
Balta, Buelent
Ozturk, Cem
Aviyente, Viktorya
Vincent, Mark A.
Hillier, Ian H.
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13): : 4800 - 4809
[34] Claisen rearrangements of benzyl vinyl ethers: theoretical investigation of mechanism, substituent effects, and regioselectivity
Krenske, Elizabeth H.
Burns, Jed M.
McGeary, Ross P.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (37) : 7887 - 7893
[35] Wittig olefination: An efficient route for the preparation of allyl vinyl ethers - Precursors for the Claisen rearrangement
Kulkarni, MG
Pendharkar, DS
Rasne, RM
TETRAHEDRON LETTERS, 1997, 38 (08) : 1459 - 1462
[36] ASYMMETRIC CLAISEN REARRANGEMENT OF CIS-ALLYLIC VINYL ETHERS WITH CHIRAL ORGANOALUMINUM REAGENT
MARUOKA, K
YAMAMOTO, H
SYNLETT, 1991, (11) : 793 - 794
[37] Synthesis of allenes through triazole gold(III) catalysed rearrangement of propargyl vinyl ethers
Wang, Dawei
Yang, Yongchun
Huang, Ronghui
Wang, Likui
Wan, Huida
JOURNAL OF CHEMICAL RESEARCH, 2016, (11) : 645 - 647
[38] A Microwave-Assisted Domino Rearrangement of Propargyl Vinyl Ethers to Multifunctionalized Aromatic Platforms
Tejedor, David
Mendez-Abt, Gabriela
Cotos, Leandro
Ramirez, Miguel A.
Garcia-Tellado, Fernando
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (12) : 3318 - 3321
[39] Catalyzed olefin isomerization leading to highly stereoselective Claisen rearrangements of aliphatic allyl vinyl ethers
Nelson, SG
Bungard, CJ
Wang, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) : 13000 - 13001
[40] CARBANION REARRANGEMENTS IN THE GAS-PHASE - THE UNUSUAL CLAISEN REARRANGEMENT OF DEPROTONATED ALLYL VINYL ETHER
EICHINGER, PCH
BOWIE, JH
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (09) : 1479 - 1485

← 1 2 3 4 5 →