1322091-23-5Relevant articles and documents
Completely Stereoselective Synthesis of Sulfonated 1,3-Dihydroisobenzofurans via Radical Multicomponent Reactions
Shi, Hao-Nan,Huang, Min-Hua,He, Chun-Lan,Lu, Hai-Ping,Hao, Wen-Juan,Tu, Xing-Chao,Tu, Shu-Jiang,Jiang, Bo
, p. 13686 - 13695 (2019/10/16)
Two types of new oxidant-free radical multicomponent reactions of β-alkynyl ketones, aryldiazonium salts, and DABCO·(SO2)2 (DABSO) were established, leading to the tunable generation of two class of sulfonated 1,3-dihydroisobenzofurans with moderate to good yields and complete stereoselectivity under the mild conditions. The radical-induced scission/recombination of the C(sp3)-C(sp3) bond enabled direct 1,8-halosulfonylation of β-alkynyl ketones, giving 1,3-dimethylene-substituted (1Z,3Z)-1,3-dihydroisobenzofurans with substituent diversity by p-nitrobenzyl bromide (PNBB) or p-nitrobenzyl chloride (PNBC) as the halo source. Fine-tuning substituents to strong electron-withdrawing ones, such as nitro, cyano, and trifluoromethyl, linked to aryldiazonium tetrafluoroborates allowed a different annulation/1,5-azosulfonylation process to access sulfonated (Z)-1,3-dihydroisobenzofurans with one quaternary carbon-amino functionality.
Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins
Cao, Ziping,Zhu, Hongbo,Meng, Xin,Tian, Laijin,Sun, Xuejun,Chen, Guang,You, Jinmao
supporting information, p. 9125 - 9129 (2016/07/14)
An unprecedented access to strained tetracyclic bridgehead alkenes by reaction of easily accessible ortho-alkynylarylaldehydes with conjugated dienes is described. The process involves a chemo- and stereo-selective, gold-catalyzed, tandem intermolecular [3+2] cycloaddition/Prins-type ring-closing reaction that allows generating structural complexity in a straightforward manner. This approach for the preparation of anti-Bredt compounds is synthetically superior to those previously reported: the procedure is easy to implement, operates under mild experimental conditions, is efficient, and exhibits a good substrate scope.
Tuning the reactivity of Au-complexes in an Au(i)/chiral Bronsted acid cooperative catalytic system: An approach to optically active fused 1,2-dihydroisoquinolines
Patil, Nitin T.,Mutyala, Anil Kumar,Konala, Ashok,Tella, Ramesh Babu
supporting information; experimental part, p. 3094 - 3096 (2012/04/17)
An enantioselective cooperative catalysis protocol, utilizing achiral Au(i) complexes and chiral Bronsted acids, has been developed for the synthesis of optically pure fused 1,2-dihydroisoquinolines starting from 2-alkynylbenzaldehydes and 2-aminobenzamides. The Royal Society of Chemistry 2012.