Free radical-mediated vinyl amination: a mild, general pyrrolidinyl enamine synthesis
…, AL Williams, EN Prabhakaran, JN Johnston
Index: Nugent, Benjamin M.; Williams, Amie L.; Prabhakaran; Johnston, Jeffrey N. Tetrahedron, 2003 , vol. 59, # 45 p. 8877 - 8888
Full Text: HTML
Citation Number: 41
Abstract
The complete scope of free radical-mediated vinyl amination is described, using 5-exo-trig cyclizations of vinyl radicals to the nitrogen of azomethines. The focus is primarily on N, N- dialkyl enamines since their nucleophilicity renders them the most challenging enamines to synthesize using redox conditions. These studies establish several encouraging precedents for the broader application of this strategy.
Related Articles:
[Ackermann, Martin; Bucher, Janina; Rappold, Melissa; Graf, Katharina; Rominger, Frank; Hashmi, A. Stephen K. Chemistry - An Asian Journal, 2013 , vol. 8, # 8 p. 1786 - 1794]
Chelation Control through the Coordination of Lewis Acids to an Acetylenic π-Bond
[Asao, Naoki; Asano, Toru; Ohishi, Takeshi; Yamamoto, Yoshinori Journal of the American Chemical Society, 2000 , vol. 122, # 19 p. 4817 - 4818]
Synthesis of biaryls using nickel-catalyzed [2+ 2+ 2] cocyclization
[Sato, Yoshihiro; Ohashi, Kenji; Mori, Miwako Tetrahedron Letters, 1999 , vol. 40, # 28 p. 5231 - 5234]
[Hiroya, Kou; Jouka, Rumi; Kameda, Mitsuyoshi; Yasuhara, Akito; Sakamoto, Takao Tetrahedron, 2001 , vol. 57, # 48 p. 9697 - 9710]
[Praveen; Iyyappan; Girija; Kumar, K Suresh; Perumal Journal of Chemical Sciences, 2012 , vol. 124, # 2 p. 451 - 462]