15341-64-7Relevant articles and documents
Gold-Catalyzed Synthesis of 2,5-Disubstituted Oxazoles from Carboxamides and Propynals
Xu, Yun,Wang, Qian,Wu, Yufeng,Zeng, Zhongyi,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 2309 - 2314 (2019/04/13)
2,5-Disubstituted oxazoles are synthesized by oxidative gold catalysis. In contrast to a reported procedure that delivers 2,4-disubstituted oxazoles starting from terminal alkynes, a switch in selectivity towards a 2,5-disubstitution is achieved by the use of propynals as starting materials. In the new reaction, the key intermediate is formed by the nucleophilic attack of the carboxamide onto a gold carbenoid, and then condensates with the more electrophilic aldehyde moiety already present in the substrate and not with the ketone that is derived from the oxygen donor. This new cyclization mode introduces a new carbonyl moiety as substituent at the 2,5-disubstituted oxazole, an attractive motive that can be found in bioactive compounds or be used for further derivatizations. (Figure presented.).
Reactivity of indole-3-alkoxides in the absence of acids: Rapid synthesis of homo-bisindolylmethanes
Chinta, Bhavani Shankar,Baire, Beeraiah
, p. 8106 - 8116 (2016/11/22)
An unprecedented behaviour of in situ generated indole-3-alkoxides (MgX or Li) has been reported. Tuning the electronic properties of the alkoxides offered the direct and selective construction of bisindolylmethanes and indole-3-carbinols. This process shows very broad scope and represents the reagent (external) free, greener synthesis of structurally divergent bisindolylmethanes.
Copper-Catalyzed Propargylic Substitution of Dichloro Substrates: Enantioselective Synthesis of Trisubstituted Allenes and Formation of Propargylic Quaternary Stereogenic Centers
Li, Hailing,Grassi, David,Guénée, Laure,Bürgi, Thomas,Alexakis, Alexandre
supporting information, p. 16694 - 16706 (2016/02/12)
An easy and versatile Cu-catalyzed propargylic substitution process is presented. Using easily prepared prochiral dichloro substrates, readily available Grignard reagents together with catalytic amount of copper salt and chiral ligand, we accessed a range of synthetically interesting trisubstituted chloroallenes. Substrate scope and nucleophile scope are broad, providing generally high enantioselectivity for the desired 1,3-substitution products. The enantioenriched chloroallenes could be further transformed into the corresponding trisubstituted allenes or terminal alkynes bearing all-carbon quaternary stereogenic centers, through the copper-catalyzed enantiospecific 1,1/1,3-substitutions. The two successive copper-catalyzed reactions could be eventually combined into a one-pot procedure and different desired allenes or alkynes were obtained respectively with high enantiomeric excesses.