A facile catalytic enantioselective 1,2-addition of diynes to trifluoromethyl ketones was developed. By a com- bination of Me2Zn, Ti（OPr-i）4, BaF2 and quinine, the reaction of a series of terminal diynes with triflu...A facile catalytic enantioselective 1,2-addition of diynes to trifluoromethyl ketones was developed. By a com- bination of Me2Zn, Ti（OPr-i）4, BaF2 and quinine, the reaction of a series of terminal diynes with trifluoromethyl ke- tones proceeded to afford trifluoromethylated chrial tertiary alcohols with the diyne moiety in good to high yields with moderate to high enantioselectivities. Furthermore, this catalytic asymmetric diyne addition to trifluoro- methylketone was applied in the synthesis of the Efavirenz analogue.展开更多
The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans,which features metal-free,additive-free,broad functional group tolerance,and readily accessible ...The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans,which features metal-free,additive-free,broad functional group tolerance,and readily accessible starting materials.Notably,this strategy is applicable in both intramolecular and intermolecular protocols.Mechanistic studies suggested that the reactions undergo a cyclopropanation/rearrangement sequence.With an E/E-1,3-dienal,corresponding N-tosylhydrazones were readily prepared and subjected to phenylboronic acid to form a double bond migration product and indoles to construct a five-member ring via [3 + 2] annulation reaction.展开更多
文摘A facile catalytic enantioselective 1,2-addition of diynes to trifluoromethyl ketones was developed. By a com- bination of Me2Zn, Ti（OPr-i）4, BaF2 and quinine, the reaction of a series of terminal diynes with trifluoromethyl ke- tones proceeded to afford trifluoromethylated chrial tertiary alcohols with the diyne moiety in good to high yields with moderate to high enantioselectivities. Furthermore, this catalytic asymmetric diyne addition to trifluoro- methylketone was applied in the synthesis of the Efavirenz analogue.
基金supported by the National Natural Science Foundation (21772046, 21931013)Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University。
文摘The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans,which features metal-free,additive-free,broad functional group tolerance,and readily accessible starting materials.Notably,this strategy is applicable in both intramolecular and intermolecular protocols.Mechanistic studies suggested that the reactions undergo a cyclopropanation/rearrangement sequence.With an E/E-1,3-dienal,corresponding N-tosylhydrazones were readily prepared and subjected to phenylboronic acid to form a double bond migration product and indoles to construct a five-member ring via [3 + 2] annulation reaction.
