Author : David Thomas Amos
Publisher :
ISBN 13 :
Total Pages : 367 pages
Book Rating : 4.:/5 (55 download)
Book Synopsis Synthesis of Nitrogen Heterocycles Via the Intramolecular [4+2] Cycloaddition of Iminoacetonitriles by : David Thomas Amos
Download or read book Synthesis of Nitrogen Heterocycles Via the Intramolecular [4+2] Cycloaddition of Iminoacetonitriles written by David Thomas Amos and published by . This book was released on 2003 with total page 367 pages. Available in PDF, EPUB and Kindle. Book excerpt: Iminoacetonitriles have been shown to function as aza dienophiles in intramolecular Diels-Alder reactions, affording substituted quinolizidines and indolizidines. The cycloadducts are formed with a high preference for an exo-orientated cyano group due to the a-amino nitrile anomeric effect. The substrates for these [4+2] cycloadditions are prepared from readily available alcohols via a Mitsunobu reaction with the previously unknown N-cyanomethyltriflamide (HN(Tf)CH2CN) followed by cesium carbonate promoted elimination of trifluoromethanesulfinate. The a-amino nitrile cycloadducts are versatile synthetic intermediates and can be elaborated via alkylation, reduction, and nucleophilic addition chemistry to provide a variety of substituted and functionalized nitrogen heterocycles. Initial investigations have been undertaken to explore the use of this methodology in the total synthesis of alkaloid natural products.