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Monday, August 24 • 4:00pm - 4:20pm
[0092] Stereoselective Synthesis of Oxa- and Aza-cycles using Reactions of Alkynes

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In recent years, metal catalysed transformations of alkynes have gain prominence for the synthesis of oxa- and aza-cycles. However, their utility under metal free conditions is still under explored. In a programme directed at the stereoselective synthesis of oxa- and aza-cycles using vinylogous carbonates and carbamates, we demonstrated that the oxonium and iminium ion intermediates generated from these functional groups in the presence of Lewis acids can be trapped with alkynes giving stereoselective access to functionalized 2,3-disubstituted dihydrobenzofurans and indoline derivatives. The regioselectivity of alkyne iminium ion cyclization can be reversed using a tethered hydroxy group as nucleophile. Further, we have also developed divergent synthesis of N-fused indolylidine, indole, and indoline derivatives using alkyne-iminium ion cyclisation. Interestingly, trapping of vinyl cation intermediate generated after alkyne iminium ion cyclisation was found to be dependent on the Lewis/Bronsted acid and solvent used. This talk will highlight some details of these studies.


ST Lecturers
avatar for Santosh J. Gharpure

Santosh J. Gharpure

Associate Professor, Indian Institute of Technology Bombay, India
Dr. Santosh J. Gharpure graduated with an M.Sc. degree in 1996, from Indian Institute of Technology Bombay, Powai. He obtained Ph.D. from Indian Institute of Science, Bangalore working with Late Prof. A. Srikrishna in 2001. He held a post-doctoral position with Prof. P. Andrew Evans at Indiana University, Bloomington, U.S.A. Subsequently; he joined the Department of Chemistry, IIT Madras, Chennai in the year 2004. In 2012, he moved to... Read More →



Monday August 24, 2015 4:00pm - 4:20pm
Girvetz 2115