Domino reactions in water for the stereoselective synthesis of novel spiro dihydro-2′H-[indene-2,3′-thiophen]-1(3H)-ones with three contiguous stereocenters |
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Authors: | Sundaravel Vivek Kumar Pitchaimani PrasannaSubbu Perumal |
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Institution: | Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India |
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Abstract: | The domino reactions of (E)-2-(aryl)-2,3-dihydro-1H-inden-1-ones and 1,4-dithiane-2,5-diol in the presence of triethylamine in water stereoselectively afforded a library of 2′-(aryl)-4′-hydroxy-4′,5′-dihydro-2′H-spiroindene-2,3′-thiophen]-1(3H)-ones. This transformation presumably proceeds via the generation of 2-mercaptoacetaldehyde from 1,4-dithiane-2,5-diol followed by Michael addition–intramolecular aldol sequence with C–C and C–S bond formations and creation of three contiguous stereocenters in a one-pot operation. |
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Keywords: | Domino reactions (E)-2-(Aryl)-2 3-dihydro-1H-inden-1-one 1 4-Dithiane-2 5-diol 2&prime -(Aryl)-4&prime -hydroxy-4&prime 5&prime -dihydro-2&prime H-spiro[indene-2 3&prime -thiophen]-1(3H)-one Stereoselectivity |
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