Stereoselective Epoxidation of Cyclic Dienes and Trienes by Dioxiranes

被引：3

作者：

D'Accolti, Lucia ^{[1
]}

Annese, Cosimo ^{[1
]}

Aresta, Antonella ^{[1
]}

Fusco, Caterina ^{[2
]}

机构：

[1] Univ Bari A Moro, Dipartimento Chim, I-70126 Bari, Italy

[2] Univ Bari, Dipartimento Chim, CNR ICCOM, I-70126 Bari, Italy

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2014年 / 51卷 / 05期

关键词：

DIMETHYLDIOXIRANE; REACTIVITY; OXIDATIONS; CONVERSION; ALCOHOLS;

D O I：

10.1002/jhet.1839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxides are essential building blocks in organic chemistry. The epoxidation of unsubstituted cyclic dienes 2, 3, 4 and triene 5 using dimethyldioxirane (1a) and its trifluoro analog 1b methyl(trifluoromethyl)dioxirane has been investigated. The excellent yields obtained (90-98%) are accompanied by outstandingly high diastereoselectivities (90-98%). Interpretation of results based upon the early idea that polar groups can direct the dioxirane attack by dipole-dipole interaction provides a likely rationale, along with a more generalized mechanistic view.

引用

页码：1482 / 1486

页数：5

共 44 条

[21] Stereoselective Amine Addition to Six-Membered Cyclic Nitronates Promoted by Silyl Triflate
Mikhaylov, Andrey A.
Dilman, Alexander D.
Khomutova, Yulia A.
Arkhipov, Dmitry E.
Korlyukov, Alexander A.
Ioffe, Sema L.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) : 5670 - 5677
[22] Pseudo-Five-Component Stereoselective Synthesis of Highly Functionalized 3-Azabicyclo[3.3.1]nona-2,7-dienes
Ismiyev, A. I.
Dotsenko, V. V.
Aksenov, N. A.
Aksenova, I., V
Magarramov, A. M.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2021, 91 (05) : 758 - 767
[23] Cyclic(alkyl)(amino)carbene ruthenium complexes for Z-stereoselective (asymmetric) olefin metathesis
Morvan, Jennifer
Vermersch, Francois
Lorkowski, Jan
Talcik, Jakub
Vives, Thomas
Roisnel, Thierry
Crevisy, Christophe
Vanthuyne, Nicolas
Bertrand, Guy
Jazzar, Rodolphe
Mauduit, Marc
CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (02) : 381 - 388
[24] Copper-Catalyzed, Stereoselective Cross-Coupling of Cyclic Allyl Boronic Acids with α-Diazoketones
Wang, Dong
Szabo, Kalman J.
ORGANIC LETTERS, 2017, 19 (07) : 1622 - 1625
[25] Niobium-silica catalysts for the selective epoxidation of cyclic alkenes: the generation of the active site by grafting niobocene dichloride
Tiozzo, Cristina
Bisio, Chiara
Carniato, Fabio
Gallo, Alessandro
Scott, Susannah L.
Psaro, Rinaldo
Guidotti, Matteo
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (32) : 13354 - 13362
[26] Base-Induced Sulfoxide-Sulfenate Rearrangement of 2-Sulfinyl Dienes for the Regio- and Stereoselective Synthesis of Enantioenriched Dienyl Diols
Velado, Marina
Martinovic, Manuel
Alonso, Ines
Tortosa, Mariola
de la Pradilla, Roberto Fernandez
Viso, Alma
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06) : 3697 - 3713
[27] Wittig Olefination between Phosphine, Aldehyde, and Allylic Carbonate: A General Method for Stereoselective Synthesis of Trisubstituted 1,3-Dienes with Highly Variable Substituents
Zhou, Rong
Wang, Chunzhang
Song, Haibin
He, Zhengjie
ORGANIC LETTERS, 2010, 12 (05) : 976 - 979
[28] Stereoselective synthesis of 1,3,5-trienes from alkynones and allyl carbonyl compounds through C-C σ-bond cleavage under transition-metal-free conditions
Cheng, Lu
Wang, Mengdan
Yang, Yajie
Wang, Zongkang
Zhu, Yilin
Kong, Lingkai
Li, Yanzhong
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (12): : 3354 - 3359
[29] Synthesis of Stereoselective Multifused Cyclic Compounds via Palladium-Catalyzed C3-Allylative Dearomatization
Im, Juno
Jung, Jiyun
Park, Hanbin
Kim, Taehwan
Kang, Min Jae
Yoo, Eun Jeong
ACS CATALYSIS, 2023, 14 (01) : 153 - 160
[30] Asymmetric trans-dihydroxylation of cyclic olefins by enzymatic or chemo-enzymatic sequential epoxidation and hydrolysis in one-pot
Xu, Yi
Li, Aitao
Jia, Xin
Li, Zhi
GREEN CHEMISTRY, 2011, 13 (09) : 2452 - 2458

← 1 2 3 4 5 →