2185014-90-6Relevant articles and documents
Asymmetric Cyclization/Nucleophilic Tandem Reaction of o-Alkynylacetophenone with (Diazomethyl)phosphonate for the Synthesis of Functional Isochromenes
Cai, Liu,Chen, Yuan,Cao, Hao,Wei, Qi,Yang, Yi,Ouyang, Qin,Peng, Yungui
, p. 7597 - 7601 (2019)
An efficient asymmetric reaction between (diazomethyl)phosphonate with o-alkynylacetophenone has been established by employing different stereocontrol strategy. A variety of isochromenes bearing tetrasubstituted stereocenters and (diazomethyl)phosphonate at the 1-position were prepared in yield up to 99% with enantioselectivity up to 94% enantiomeric excess (ee) for the first time. These functional isochromenes could be transformed to important structural motifs in biologically active compounds. Moreover, density functional theory calculations were conducted to gain insight into the process and the stereoselectivity.
Copper-Catalyzed Enantioselective Arylative Desymmetrization of Prochiral Cyclopentenes with Diaryliodonium Salts
Wu, Hua,Wang, Qian,Zhu, Jieping
supporting information, p. 2721 - 2725 (2018/02/09)
A copper-catalyzed enantioselective arylative desymmetrization of prochiral cyclopentenes with diaryliodonium salts was developed. In the presence of a catalytic amount of a chiral copper–bisoxazoline complex, which was generated in situ, the reaction of 4-substituted or 4,4-disubstituted cyclopent-1-enes with diaryliodonium hexafluoroarsenates afforded the chiral arylated products in good yields with excellent enantioselectivity. A cyclohexyl-containing Box ligand was essential for the high enantioselectivity. Transformation of the enantiomerically enriched adducts into other chiral building blocks is also documented.
