Intramolecular Cyclization of ortho-Substituted Chalcones in the Presence of Palladium Complexes with Chiral Bisphosphine Ligands

被引：3
|
作者：
Ashatkina, M. A. [1 ]
Reznikov, A. N. [1 ]
Klimochkin, Yu N. [1 ]
机构：
[1] Samara State Tech Univ, Samara 443100, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 58卷 / 05期
基金：
俄罗斯科学基金会;
关键词：
asymmetric synthesis; ortho-substituted chalcones; chiral ligands; palladium complexes; catalysis; ASYMMETRIC CONJUGATE ADDITION; ELECTRON-RICH OLEFINS; HECK REACTION; ORGANOMETALLIC REAGENTS; BITE ANGLE; ARYLATION; ENONES; ACIDS;
D O I：
10.1134/S1070428022050116
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The influence of the ligands and leaving group on the direction and selectivity of the intramolecular arylation of ortho-substituted chalcones is discussed. In the presence of Pd complexes with (R)-BINAP, (R)-C-3-TuncPhos, and (S,S '',R,R')-TangPhos ligands, 3-phenylindan-1-one was obtained with an enantiomeric excess of up to 83%. Along with the reductive cyclization product, 2-methyl-3-phenyl-1H-inden-1-one is formed. The cyclization of ortho-mesyloxy- and methoxycarbonyloxy-substituted chalcones under similar conditions gives rise to 2-phenylchroman-4-one.
引用
收藏
页码：710 / 719
页数：10
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