Autoxidative Annulation of the a-Cyano p-TMS-capped Alkynyl Cycloalkanone System. Discovery of A Novel Synthetic Reaction in Organic Chemistry

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Title:	Autoxidative Annulation of the a-Cyano p-TMS-capped Alkynyl Cycloalkanone System. Discovery of A Novel Synthetic Reaction in Organic Chemistry
Authors:	Ying-Chieh Wong (翁英傑) Min-Tsang Hsieh Prashanth K. Amancha Chih-Lung Chin Cheng-Feng Liao Chun-Wei Kuo (夏克山)
Date:	2011
Issue Date:	2011-06-23 14:57:42 (UTC+8)
Abstract:	During the course of our studies on a-activated cross conjugated cycloalkenone systems in organic synthesis, we have serendipitously discovered that compound 2, obtained through 1,4-conjugate addition of l-(trimethylsilyl)-l-butyn-4-yl magnesium chloride to a-cyano cyclohexenone 1, could undergo autoxidative annulation upon exposure to air and light to afford cyclic products 3 and 4, respectively (Figure 1). To optimize reaction conditions, reaction parameters, including solvents, bases and time, were systematically varied and monitored. As a result, the system (pyridine (catalyst)/02 (1 atm)/rt) is found to be the method of choice to effect the observed autoxidative reaction. On the basis of this newly developed protocol, a variety of highly functionalized bicyclic frameworks can be effectively constructed in moderate to good yields as illustrated in Scheme 1.
Relation:	2011年台俄有機、藥物與生物化學交流暨藥物化學研討會，起迄日：2011/04/06~2011/04/05，地點：溪頭台大實驗林
Appears in Collections:	[Pharmacy and Science] 2011 Taiwanese-Russian Organic, Medicinal and Bio Chemistry Interactions & PST Medicinal Chemistry Symposium

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