HIGHLY ACTIVE RHODIUM CATALYST WITH ELECTRON-POOR DIPHOSPHINE ENABLES EFFICIENT SYNTHESIS OF CHIRAL 4-ARYL-δ-LACTONES

被引：19
|
作者：
Korenaga, Toshinobu [1 ]
Maenishi, Ryota [1 ]
Osaki, Kazutaka [1 ]
Sakai, Takashi [1 ]
机构：
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Chem & Biochem, 3-1-1 Tsushima Naka, Okayama 7008530, Japan
来源：
HETEROCYCLES | 2010年 / 80卷 / 01期
关键词：
Chiral Lactone; Rhodium Catalyst; Electron-Poor Ligand; Asymmetric 1,4-Addition; Boronic Acid; ASYMMETRIC 1,4-ADDITION; ARYLBORONIC ACIDS; ORGANOBORONIC ACIDS; CONJUGATE ADDITION; BORONIC ACIDS; LIGANDS; ARYL;
D O I：
10.3987/COM-09-S(S)40
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral 4-aryl-delta-lactones could be synthesized efficiently with high enantioselectivity through asymmetric 1,4-addition of arylboronic acid to alpha,beta-unsaturated lactones using Rh catalyst including electron-poor diphosphine (MeO-F-12-BIPHEP) at room temperature for 1 h. In particular, our catalytic system proved to be applicable to relatively large coumarin analogues, giving optically pure 4-phenylchroman-2-one analogues in a short time.
引用
收藏
页码：157 / 162
页数：6
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