1379786-11-4Relevant academic research and scientific papers
A Catalyst-Controlled Enantiodivergent Bromolactonization
Chan, Yuk-Cheung,Lam, Ying-Pong,Tse, Ying-Lung Steve,Wang, Xinyan,Wong, Jonathan,Yeung, Ying-Yeung
supporting information, p. 12745 - 12754 (2021/08/30)
A catalyst-controlled enantiodivergent bromolactonization of olefinic acids has been developed. Quinine-derived amino-amides bearing the same chiral core but different achiral aryl substituents were used as the catalysts. Switching the methoxy substituent in the aryl amide system from meta- to ortho-position results in a complete switch in asymmetric induction to afford the desired lactone in good enantioselectivity and yield. Mechanistic studies, including chemical experiments and density functional theory calculations, reveal that the differences in steric and electronic effects of the catalyst substituent alter the reaction mechanism.
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
Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst
Tan, Chong Kiat,Le, Chencheng,Yeung, Ying-Yeung
, p. 5793 - 5795 (2012/08/08)
A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed. The use of the enantio-enriched lactones in the synthesis of chiral synthetic intermediates is also demonstrated. 2012
