Tetrahedron letters

Competitive intramolecular aminolysis: Relative rates of 5-and 6-membered lactam ring closure

KH Patterson, GJ Depree, JA Zender, PJ Morris

Index: Patterson, Kevin H.; Depree, Gary J.; Zender, Johannes A.; Morris, Peter J. Tetrahedron Letters, 1994 , vol. 35, # 2 p. 281 - 284

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Citation Number: 7

Abstract

Abstract Methyl 4, 5-diaminopentanoate (4, 5-Dape Me) undergoes competitive intramolecular aminolysis to 5-aminomethyl-2-pyrrolidinone (L5) and 5-amino-2- piperidinone (L6) in dilute alkaline aqueous solution at 25 C. Use of this single compound provides an ideal case for assessing the relative rates of 5-and 6-membered lactam ring closure. Assessments are also made using the intramolecular aminolysis of pairs of ...