51431-59-5Relevant articles and documents
Practical synthesis of aromatic bisabolanes: Synthesis of 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid
Ishigami, Ken,Katsuta, Ryo,Murakawa, Hazuki,Saito, Tatsuo,Shiotani, Nanami,Shirakawa, Izumi,Ueda, Kazuya,Yajima, Arata
supporting information, (2021/06/12)
The enantioselective synthesis of aromatic bisabolanes, such as 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid, has been described. Our methodology for the total synthesis of aromatic bisabolanes involves the stereoselective const
Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters
Cai, Aijie,Kleij, Arjan W.
supporting information, p. 14944 - 14949 (2019/11/05)
We describe here the first general asymmetric synthesis of sterically encumbered α,α-disubstituted allylic sulfones via Pd-catalyzed allylic substitution. The design and application of a new and highly efficient phosphoramidite ligand (L10) proved to be crucial, and a wide variety of challenging allylic sulfones featuring quaternary stereocenters could be obtained in good yields and with good to excellent levels of regio- and enantioselectivities under attractive process conditions. The developed methodology employs easily accessible chemical feedstock including racemic allylic precursors and sodium sulfinates. The utility of the method is further demonstrated by the synthesis of the sesquiterpene (?)-Agelasidine A.
Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates
Grassi, David,Alexakis, Alexandre
supporting information, p. 3171 - 3186 (2015/11/03)
Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.