Yıl 2019, Cilt 14 , Sayı 2, Sayfalar 436 - 441 2019-11-30

Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction
Asimetrik Hetero Diels-Alder Reaksiyonu için Organaokatalizör Olarak Kiral 1,4-Hidroksiarilalkoller (HAROL) ve 1,4-Aminoalkilfenoller (AAP)

Erkan ERTÜRK [1] , Mustafa Ali TEZEREN [2] , Tahir TİLKİ [3]


In this study, two chiral 2-(2-hydroxyaryl) alcohols (HAROLs; 1,4-diols) and a 1,4-aminoalkylphenol (AAP) were examined as hydrogen-bond donor (HBD) organocatalysts in the asymmetric hetero Diels-Alder (HDA) reaction of aldehydes with Rawal’s diene. Catalytic amount (10 mol%) of the both scaffolds (HAROL and AAP) have been found to effect the HDA reaction in a quite efficient manner. Among them, a HAROL molecule based on indan backbone was turned out to be the best in terms of catalytic activity and enantioselectivity. On the other hand, AAP tested seemed to act as a bifunctional organocatalyst, i.e. as both a Lewis base and HBD organocatalyst. Experimental results underpins that a careful tuning of HAROL structure might lead to the development of more general HBD organocatalysts.

Bu çalışmada, iki tane kiral 2-(2-hidroksiaril) alkol (HAROL, 1,4-diol) ve bir 1,4-aminoalkilfenol (AAP), aldehitlerin Rawal dieni ile asimetrik hetero Diels-Alder (HDA) reaksiyonunda hidrojen-bağı donörü (HBD) organokatalizörleri olarak incelenmiştir. Her iki yapının (HAROL ve AAP) katalitik miktarının (%10) HDA reaksiyonunu oldukça verimli bir şekilde gerçekleştirdiği bulunmuştur. Bunlar arasında, indan iskeleti bazlı bir HAROL molekülünün, katalitik aktivite ve enantioseçicilik bakımından en iyisi olduğu ortaya çıkmıştır. Öte yandan, test edilen AAP bifonksiyonlu bir organokatalizör olarak, diğer bir deyişle bir Lewis bazı ve HBD organokatalizörü gibi davranıyor görünmektedir. Deneysel sonuçlar HAROL yapısının dikkatli bir şekilde ayarlanmasının, daha genel HBD organokatalizörlerinin geliştirilmesine yol açabileceğini desteklemektedir.

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Birincil Dil en
Konular Mühendislik, Kimya
Bölüm Makaleler
Yazarlar

Orcid: 0000-0001-5746-5683
Yazar: Erkan ERTÜRK (Sorumlu Yazar)
Kurum: TÜBİTAK Marmara Araştırma Merkezi, Kimyasal Teknoloji Enstitüsü
Ülke: Turkey


Orcid: 0000-0001-8209-7579
Yazar: Mustafa Ali TEZEREN
Kurum: SÜLEYMAN DEMİREL ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ, KİMYA BÖLÜMÜ
Ülke: Turkey


Orcid: 0000-0002-1040-2375
Yazar: Tahir TİLKİ
Kurum: SÜLEYMAN DEMİREL ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ, KİMYA BÖLÜMÜ
Ülke: Turkey


Destekleyen Kurum TÜBİTAK ARDEB ve Süleyman Demirel Üniversitesi BAP
Proje Numarası TÜBİTAK Proje No: 111T597, Süleyman Demirel Üniversitesi BAP Proje No: 4072-D1-14
Teşekkür We would like to thank both the Scientific and Technological Research Council of Turkey (grant no. 111T597) and Süleyman Demirel University (BAP project no. 4072-D1-14) for their financial supports.
Tarihler

Yayımlanma Tarihi : 30 Kasım 2019

Bibtex @araştırma makalesi { sdufeffd649920, journal = {Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi}, issn = {}, eissn = {1306-7575}, address = {}, publisher = {Süleyman Demirel Üniversitesi}, year = {2019}, volume = {14}, pages = {436 - 441}, doi = {10.29233/sdufeffd.649920}, title = {Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction}, key = {cite}, author = {ERTÜRK, Erkan and TEZEREN, Mustafa Ali and TİLKİ, Tahir} }
APA ERTÜRK, E , TEZEREN, M , TİLKİ, T . (2019). Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction. Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi , 14 (2) , 436-441 . DOI: 10.29233/sdufeffd.649920
MLA ERTÜRK, E , TEZEREN, M , TİLKİ, T . "Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction". Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 14 (2019 ): 436-441 <https://dergipark.org.tr/tr/pub/sdufeffd/issue/50336/649920>
Chicago ERTÜRK, E , TEZEREN, M , TİLKİ, T . "Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction". Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 14 (2019 ): 436-441
RIS TY - JOUR T1 - Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction AU - Erkan ERTÜRK , Mustafa Ali TEZEREN , Tahir TİLKİ Y1 - 2019 PY - 2019 N1 - doi: 10.29233/sdufeffd.649920 DO - 10.29233/sdufeffd.649920 T2 - Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi JF - Journal JO - JOR SP - 436 EP - 441 VL - 14 IS - 2 SN - -1306-7575 M3 - doi: 10.29233/sdufeffd.649920 UR - https://doi.org/10.29233/sdufeffd.649920 Y2 - 2019 ER -
EndNote %0 Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction %A Erkan ERTÜRK , Mustafa Ali TEZEREN , Tahir TİLKİ %T Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction %D 2019 %J Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi %P -1306-7575 %V 14 %N 2 %R doi: 10.29233/sdufeffd.649920 %U 10.29233/sdufeffd.649920
ISNAD ERTÜRK, Erkan , TEZEREN, Mustafa Ali , TİLKİ, Tahir . "Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction". Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 14 / 2 (Kasım 2019): 436-441 . https://doi.org/10.29233/sdufeffd.649920
AMA ERTÜRK E , TEZEREN M , TİLKİ T . Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction. SDÜFEFFD. 2019; 14(2): 436-441.
Vancouver ERTÜRK E , TEZEREN M , TİLKİ T . Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction. Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi. 2019; 14(2): 441-436.