Reactivity of alicyclic 1,5,9-triketones toward five-, six-, and seven-membered rings in acidic medium. Stereochemistry of intramolecular cyclization products

被引：0

作者：

Taisia I. Akimova

Olga A. Soldatkina

Andrey V. Gerasimenko

Vyacheslav G. Savchenko

Alevtina A. Kapustina

机构：

[1] School of Natural Sciences,

[2] Far Eastern Federal University,undefined

[3] Institute of Chemistry,undefined

[4] Far East Branch of the Russian Academy of Sciences,undefined

来源：

Chemistry of Heterocyclic Compounds | 2021年 / 57卷

关键词：

alicyclic 1,5,9-triketones; diastereomers; hemiacetals; diastereoselectivity; intramolecular cyclization;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Among nine alicyclic 1,5,9-triketones with differently fused 5-, 6-, and 7-membered rings in the molecule, existing as mixtures of 3–6 diastereomers, only those containing at least two 6-membered rings were capable of intramolecular cyclization in acidic medium (HCl, EtOH). The diastereomer mixture underwent stereoselective transformation, giving one major cyclization product. The relative configuration of chiral centers in cyclization products obtained under acidic or basic conditions was compared by X-ray crystallography. The differences were caused by divergent stereochemical outcome at the first stage of cyclization.

引用

页码：1079 / 1085

页数：6

共 5 条

[1] Reactivity of alicyclic 1,5,9-triketones toward five-, six-, and seven-membered rings in acidic medium. Stereochemistry of intramolecular cyclization products
Akimova, Taisia I.
Soldatkina, Olga A.
Gerasimenko, Andrey V.
Savchenko, Vyacheslav G.
Kapustina, Alevtina A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (11) : 1079 - 1085
[2] A new synthetic approach to 3-methylene-1-cyclohexanols fused to five-, six- and seven-membered carbocycles through intramolecular cyclization of epoxyallylsilanes
Barbero, Asuncion
Castreno, Pilar
Pulido, Francisco J.
Val, Patricia
Gonzalez-Ortega, Alfonso
Carmen Sanudo, M.
ARKIVOC, 2010, : 274 - 287
[3] Synthesis of Five-, Six-, and Seven-Membered 1,3-and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols
Deka, Manash J.
Indukuri, Kiran
Sultana, Sabera
Borah, Madhurjya
Saikia, Anil K.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4349 - 4359
[4] Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
Yang, Xuejin
Shi, Xueliang
Aratani, Naoki
Goncalves, Theo P.
Huang, Kuo-Wei
Yamada, Hiroko
Chi, Chunyan
Miao, Qian
CHEMICAL SCIENCE, 2016, 7 (09) : 6176 - 6181
[5] Diastereoselective synthesis of three-, five-, six-, and seven-membered rings from Fischer carbene complexes and 4-unsubstituted 1-amino-1,3-dienes
Aznar, Fernando
Fananas-Mastral, Martin
Alonso, Jorge
Fananas, Francisco J.
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) : 325 - 332

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