Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp<sup>3</sup>)–H Bond Functionalization
作者:Miyabi Kataoka、Yuna Otawa、Natsuki Ido、Keiji Mori
DOI:10.1021/acs.orglett.9b03498
日期:2019.12.6
diastereoselective synthesis of medium-sized carbocycle-fused piperidines via [1,n (n = 6, 7)]-[1,5]-sequential hydride shift triggered double C(sp3)–H bond functionalization. When cinnamylidene malonates having N,N-dibenzyl propylamine moiety were treated with 5 mol % of Yb(OTf)3, a [1,6]-[1,5]-sequential hydride shift/cyclization process proceeded to afford seven-membered carbocycle-fused piperidines with excellent
Palladium-Catalyzed Intramolecular C−O Bond Formation
作者:Shin-itsu Kuwabe、Karen E. Torraca、Stephen L. Buchwald
DOI:10.1021/ja012046d
日期:2001.12.1
A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction. and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile,
A High-Yield, General Method for the Catalytic Formation of Oxygen Heterocycles
作者:Karen E. Torraca、Shin-Itsu Kuwabe、Stephen L. Buchwald