Synthesis of new chiral phosphorous- and nitrogen-containing ligands from resin acids

Abstract

Starting from the phytogenic diterpenes, chiral phosphine, urea, and thiourea derivatives were synthesized. Using these new chiral ligands, Rh(I) and Ru(II) complexes were prepared and used as catalysts for the catalytic asymmetric hydrogenation of unsaturated carboxylic acids and asymmetric hydrogen-transfer reduction of carbonyl compounds. Although the enantiopurity of the products obtained was not high, it was demonstrated that chiral ligands derived from diterpenes could be used for asymmetric reduction.

Synthesis of Rosin Derived Chiral derivatizing agents for31P NMR assays of amine or alcohol and amino alcohol enantiomers

“…选择松香具有几个特点: (1)原料来源充足, 天然多 手性碳结构, 不存在对映体, 光学纯单体简便易得 [9] ; (2)有稳定构型的多环手性骨架对常规化学反应稳定, 结构上有多个官能团便于进一步结构改造 [10] ; (3)醇类作 为手性助剂制备的烷氧膦衍生试剂较稳定, 可以衍生的 底物类型较烷胺基膦试剂的更多 [11] 对称催化结果提供参考 [12～14] . 为此, 根据文献方法 [7] 以脂松香为原料通过 Diels- [15] .…”

Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis

“…1. Dehydroabietic acid (Compound 1, the starting material), and (1R, 4aS,10aR)-1,4a-dimethyl-7-isopropyl-1,2,3,4,4a,9,10, 10a-octahydrophenanthren-1-amine (Compound 2) were prepared and characterized as described in literature [14,15].…”

Direct Assembly of Polysubstituted Propiolamidinates via Palladium-Catalyzed Multicomponent Reaction of Isocyanides

“…α-Methylbenzylamine ( 1am ) was initially tested in this reaction, and the desired product 4am was isolated in 65% yield. Notably, when the dehydroabietic amine 1an , a multifunctional amine widely used in the rubber industry, food manufacturing, and exploration of chiral reagents, was subjected to this transformation, the functionalization product 4an could be obtained in 84% yield, suggesting the potential applications in modification of complex molecular skeletons.…”