1354004-75-3Relevant academic research and scientific papers
Catalyst-Controlled Regio- and Stereoselective Bromolactonization with Chiral Bifunctional Sulfides
Shirakawa, Seiji,Tsuchihashi, Ayano
, p. 1662 - 1666 (2019)
Highly regioselective 5- exo bromolactonizations of stilbene-type carboxylic acids bearing electron-withdrawing substituents are achieved for the first time via the use of chiral bifunctional sulfide catalysts possessing a urea moiety. The chiral phthalide products are obtained in moderate to good enantioselectivities as the result of 5- exo cyclizations.
Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio-, Diastereo-, and Enantioselective Bromolactonization
Nishiyori, Ryuichi,Tsuchihashi, Ayano,Mochizuki, Ayaka,Kaneko, Kazuma,Yamanaka, Masahiro,Shirakawa, Seiji
supporting information, p. 16747 - 16752 (2018/11/01)
Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under-developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio-, diastereo-, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation.
Catalytic asymmetric bromolactonization reactions using (DHQD) 2PHAL-benzoic acid combinations
Armstrong, Alan,Braddock, D. Christopher,Jones, Alexander X.,Clark, Stacy
supporting information, p. 7004 - 7008 (2013/12/04)
Catalytic (DHQD)2PHAL as modified by added benzoic acid, is an off-the-shelf catalyst-additive combination for effecting catalytic asymmetric bromolactonization reactions. This combination delivers bromolactones with asymmetric induction at a c
An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids
Chen, Jie,Zhou, Ling,Tan, Chong Kiat,Yeung, Ying-Yeung
experimental part, p. 999 - 1009 (2012/03/26)
A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4- dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.
