Diastereoselective reaction of 1,3-dihydroxy calixarene with acylisocyanates: new and easy approach for preparing inherently chiral calyx[4]arenes
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- 作者：V. I. Boyko ; A. B. Rozhenko ; V. V. Pirozhenko ; S. V. Shishkina…
- 关键词：Inherent chirality ; Calixarenes ; X ; ray structure determination ; Diastereomeric excess ; DFT
- 刊名：Structural Chemistry
- 出版年：2016
- 出版时间：February 2016
- 年：2016
- 卷：27
- 期：1
- 页码：261-272
- 全文大小：1,350 KB
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A. B. Rozhenko (1)
V. V. Pirozhenko (1)
S. V. Shishkina (2) (3)
O. V. Shishkin (2) (3)
V. I. Kalchenko (1)
1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Str. 5, Kiev, 02660, Ukraine
2. STC “Institute for Single Crystal”, National Academy of Sciences of Ukraine, Lenin Ave. 60, Kharkiv, 61001, Ukraine
3. V.N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61077, Ukraine - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Computer Applications in Chemistry
Physical Chemistry
Theoretical and Computational Chemistry - 出版者：Springer Netherlands
- ISSN：1572-9001
文摘
The facile method of generating internal chirality into the calixarene with two hydroxy groups at the lower rim via an attached chiral substituent has been proposed. The reaction with acylisocyanates, catalyzed by a small amount of triethylamine, proceeds forming predominantly one of the two possible calixarene carbamates. The best diastereomeric excess (60 %) has been achieved in the reaction of trichloroacyl isocyanates with 1,3-hydroxycalixarene substituted with the chiral phenylethyl amide moiety. The individual diastereomers of trichloroacetyl-carbamoylcalix[4]arenas were isolated by crystallization, and their absolute configuration was determined by X-ray diffraction study. The most favored conformations predicted for 1,3-dihydroxy calixarene structures by quantum chemical calculations possess very similar stability. However, the triethylamine molecule preferably connects to the one hydroxyl group of the two available ones, providing the most favorable adduct, which predominantly participates in the reaction with acylisocyanates. This gives rise to the observed diastereomeric excess. The subsequent treatment of the formed carbamoyl with n-propyl bromide in presence of NaH and hydrolysis of the product of alkylation easily provide a persistent internally chiral calixarene. Keywords Inherent chirality Calixarenes X-ray structure determination Diastereomeric excess DFT