1254701-70-6Relevant articles and documents
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.
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
