1254701-69-3Relevant 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
, p. 12745 - 12754 (2021)
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.
Enantioselective bromolactonization using an S-alkyl thiocarbamate catalyst
Jiang, Xiaojian,Tan, Chong Kiat,Zhou, Ling,Yeung, Ying-Yeung
supporting information; experimental part, p. 7771 - 7775 (2012/09/07)
The apple never falls far from the tree: S-alkyl thiocarbamate 1 (see scheme, NBP=N-bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman-Kwart rearrangement of the corresponding O-alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ-lactones in excellent yield and enantioselectivity. Copyright
Catalytic enantioselective bromolactonization of alkenoic acids in the presence of palladium complexes
Lee, Hyun Joo,Kim, Dae Young
, p. 6984 - 6986 (2013/01/15)
The catalytic enantioselective bromolactonization of alkenoic acids promoted by chiral palladium complexes has been developed, allowing facile synthesis of the corresponding γ-lactones with excellent enantioselectivity (up to 97% ee). The method reported
Asymmetric bromolactonization using amino-thiocarbamate catalyst
Zhou, Ling,Tan, Chong Kiat,Jiang, Xiaojian,Chen, Feng,Yeung, Ying-Yeung
supporting information; scheme or table, p. 15474 - 15476 (2011/02/21)
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.
