Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo [2.2. 1.02, 6] heptanes with Lead Tetraacetate

H Hu, JA Faraldos, RM Coates

Index: Hu, Huayou; Faraldos, Juan A.; Coates, Robert M. Journal of the American Chemical Society, 2009 , vol. 131, # 33 p. 11998 - 12006

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Citation Number: 15

Abstract

A series of seven cyclopent-3-en-1-ylmethylamines bearing one, two, or three methyl substituents at the C2, C3, C4, or Cα positions, including the unsubstituted parent, was accessed by ring-closing metatheses of α, α-diallylacetonitrile (or methallyl variants) and α, α- diallylacetone followed by hydride reductions or reductive amination, or by Curtius degradations of α, α-dimethyl-and 2, 2, 3-trimethylcyclopent-3-enylacetic acids. Oxidation ...