1072836-52-2Relevant academic research and scientific papers
A highly regio- and stereoselective Pd-catalyzed tandem allylic rearrangement/intramolecular decarboxylative coupling of aryl propiolates derived from Baylis-Hillman adducts
Satyanarayana, Tummanapalli,Vangapandu, Dhanunjaya Naidu,Muthuraman, Parthasarathy,Nizalapur, Shashidhar
, p. 2008 - 2013 (2015/03/30)
Abstract A highly regio- and stereoselective Pd-catalyzed tandem allylic rearrangement/intramolecular decarboxylative coupling of aryl propiolates derived from Baylis-Hillman alcohols leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes has been developed. The aryl propiolates of Baylis-Hillman alcohols derived from methyl acrylate provided exclusively (E)-1,5-diarylpent-1-en-4-ynes while the aryl propiolates of Baylis-Hillman alcohols derived from acrylonitrile provided exclusively (Z)-1,5-diarylpent-1-en-4-ynes.
Indium-mediated alkynylation of Baylis-Hillman acetates: a novel route to 1,4-enynes
Yadav, Jhillu S.,Subba Reddy, Basi V.,Yadav, Nagendra Nath,Singh, Ashutosh Pratap,Choudhary, Madavi,Kunwar, Ajit C.
scheme or table, p. 6090 - 6094 (2009/04/04)
Baylis-Hillman acetates undergo smooth alkynylation with aryl-susbstituted iodoalkynes in the presence of indium metal in refluxing dichloromethane to furnish 1,4-enynes in high yields with (E)-stereoselectivity. In the absence of Lewis acid, the reaction follows both SN2 and SN2′ pathways affording 1:1 mixtures of 1,4-enynes. Upon addition of 10 mol % of InBr3, the reaction proceeds preferably in the SN2′ manner. In the case of adducts derived from acrylonitrile, the corresponding products are obtained in fairly good yields and with (Z)-stereoselectivity.
