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Synthesis of novel chiral biquinolyl diphosphine ligand and its applications in palladium-catalyzed asymmetric allylic substitution reactions
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2016-01-30 11:50:18
Rui Zhang, Bin Xie, Guo-Shu Chen, Liqin Qiu, Yi-Xin Chen

A novel chiral diphosphine ligand, 6,6′-bis(diphenylphosphino)-5,5′-biquinoline (BIQAP) was synthesized via two step reactions using optical pure BIQOL as starting material and the molecular structure of (R)-BIQAP was determined by single-crystal X-ray diffraction. The ligand was used for Pd-catalyzed asymmetric allylic substitution reactions. High enantioselectiveties were obtained in the corresponding C–C and C–N bond formation of 1,3-diphenyl-2-propenyl acetate, with dimethyl malonate (up to 94% ee) and with potassium phthalimide (up to 96% ee).

中文翻译:

新型手性联喹啉基二膦配体的合成及其在钯催化不对称烯丙基取代反应中的应用

以光学纯BIQOL为起始原料,通过两步反应合成了一种新型的手性二膦配体6,6'-双(二苯基膦基)-5,5'-联喹啉(BIQAP),并确定了(R)-BIQAP的分子结构通过单晶X射线衍射。该配体用于Pd催化的不对称烯丙基取代反应。通过与丙二酸二甲酯(高达94%ee)和邻苯二甲酰亚胺钾(高达96%ee)的1,3-二苯基-2-丙烯基乙酸酯的相应C–C和C–N键形成,获得高对映选择性。
更新日期:2016-01-31
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