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

页码：710 / 719

页数：10

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