1197983-14-4Relevant academic research and scientific papers
Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization
Sun, Huai-Ri,Zhao, Qingyang,Yang, Hui,Yang, Sen,Gou, Bo-Bo,Chen, Jie,Zhou, Ling
supporting information, p. 7143 - 7148 (2019/09/07)
Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.
Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction
Pathak, Tejas P.,Gligorich, Keith M.,Welm, Bryan E.,Sigman, Matthew S.
supporting information; experimental part, p. 7870 - 7871 (2010/08/05)
A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.
Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation
Jensen, Katrina H.,Pathak, Tejas P.,Zhang, Yang,Sigman, Matthew S.
supporting information; experimental part, p. 17074 - 17075 (2010/03/25)
(Chemical Equation Presented) A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1.
