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Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence

หน่วยงาน Nanyang Technological University, Singapore

รายละเอียด

ชื่อเรื่อง : Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence
นักวิจัย : Komnatnyy, Vitaly V. , Givskov, Michael , Nielsen, Thomas E.
คำค้น : -
หน่วยงาน : Nanyang Technological University, Singapore
ผู้ร่วมงาน : -
ปีพิมพ์ : 2555
อ้างอิง : Komnatnyy, V. V., Givskov, M.,& Nielsen, T. E. (2012). Solid-Phase Synthesis of Structurally Diverse Heterocycles by an Amide-Ketone Condensation/N-Acyliminium Pictet-Spengler Sequence. Chemistry - A European Journal, 18(52), 16793-16800. , 0947-6539 , http://hdl.handle.net/10220/13003 , http://dx.doi.org/10.1002/chem.201202745
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : Chemistry - a European journal
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

An efficient approach for the solid-phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone–amide condensation reactions to form cyclic N-acyliminium intermediates. In the presence of a tethered nucleophile, a second cyclization reaction results in the formation of a fused bicyclic ring system. The scope of the methodology was demonstrated by several combinations of substituted ketones and nucleophiles, the latter conveniently originating from amino acids with functionalized side chains, such as tryptophan, substituted phenylalanines, and cysteine. The cyclization sequence provides diastereomerically pure products in high yields. In one extension of the methodology, the resulting relative stereochemistry of the products enables the formation of bridged ring systems by a unique cyclative release mechanism.

บรรณานุกรม :
Komnatnyy, Vitaly V. , Givskov, Michael , Nielsen, Thomas E. . (2555). Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence.
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Komnatnyy, Vitaly V. , Givskov, Michael , Nielsen, Thomas E. . 2555. "Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence".
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Komnatnyy, Vitaly V. , Givskov, Michael , Nielsen, Thomas E. . "Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence."
    กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2555. Print.
Komnatnyy, Vitaly V. , Givskov, Michael , Nielsen, Thomas E. . Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium Pictet-Spengler sequence. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2555.