Enantiopure cis- and trans -2-(2-Aminocyclohexyl)phenols: Effective Preparation, Solid-State Characterization, and Application in Asymmetric Organocatalysis
Yazarlar (5)
Mustafa A. Tezeren
Tubıtak Marmara Research Center, Türkiye
Tubıtak Marmara Research Center, Türkiye
Doç. Dr. Tolga Acar YEŞİL Tubıtak Marmara Research Center, Türkiye
Prof. Dr. Yunus Zorlu Gebze Teknik Üniversitesi, Türkiye
Prof. Dr. Tahir Tilki Süleyman Demirel Üniversitesi, Türkiye
Arş. Gör. Erkan Ertürk Tubıtak Marmara Research Center, Türkiye
| Makale Türü | Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale) | ||
| Dergi Adı | European Journal of Organic Chemistry (Q1) | ||
| Dergi ISSN | 1434-193X Dergi Bilgileri (2018) | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | İngilizce | Basım Tarihi | 11-2018 |
| Cilt / Sayı / Sayfa | 2018 / 48 / 7017–7032 | DOI | 10.1002/ejoc.201801445 |
| Makale Linki | https://doi.org/10.1002/ejoc.201801445 | ||
| UAK Araştırma Alanları |
Organik Kimya
Spektroskopi
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| Özet |
| Effective synthesis of cis‐ and trans‐2‐(2‐methoxyphenyl)cyclohexylamine as well as their multigram‐scale optical resolution by diastereomeric salt formation with dibenzoyl tartaric acid have been described. Assignment of absolute configurations to the enantiomers has been made by X‐ray crystallography. Starting from the resolved precursor, diverse aminoalkylphenols (AAPs) having primary, secondary, and tertiary amine group as well as a quaternary ammonium phenol have been prepared as potential bifunctional organocatalysts based on the cyclohexane backbone. We furthermore report herein that AAPs carrying a primary amine and a phenolic hydroxyl group can catalyze the direct aldol reaction with high activity and setereoselectivity, and thus up to 97 % yield, 90:10 syn/anti diastereomeric ratio, and 80 % enantiomeric excess can be achieved. |
| Anahtar Kelimeler |
| Aldol reactions | Asymmetric synthesis | Chiral primary amines | Chiral resolution | Organocatalysis |
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| Web of Science | 5 |
| Scopus | 4 |
| Google Scholar | 4 |