Carbon–carbon bond-forming reactions of α-carbonyl carbocations: exploration of a reversed-polarity equivalent of enolate chemistry
…, JA Dubland, MG Sarwar, MG Chudzinski, MS Taylor
Index: Lai, Ping-Shan; Dubland, Joshua A.; Sarwar, Mohammed G.; Chudzinski, Michael G.; Taylor, Mark S. Tetrahedron, 2011 , vol. 67, # 39 p. 7586 - 7592
Full Text: HTML
Citation Number: 14
Abstract
Carbon–carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid-or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an 'umpolung'of conventional enolate chemistry, and enables C–C bond construction in both intra-and intermolecular contexts. Attempts to develop diastereoselective variants of this process ...
Related Articles:
[Tetrahedron Letters, , vol. 25, # 43 p. 4943 - 4946]
Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas
[Heller, Stephen T.; Sarpong, Richmond Organic Letters, 2010 , vol. 12, # 20 p. 4572 - 4575]
[Ohshima, Takashi; Ipposhi, Junji; Nakahara, Yasuhito; Shibuya, Ryozo; Mashima, Kazushi Advanced Synthesis and Catalysis, 2012 , vol. 354, # 13 p. 2447 - 2452]
[Tetrahedron, , vol. 62, # 35 p. 8384 - 8392]
First Iodine-Catalyzed Deallylation of Reactive Allyl Methylene Esters
[Nawghare, Beena R.; Lokhande, Pradeep D. Synthetic Communications, 2013 , vol. 43, # 14 p. 1955 - 1963]