Asymmetric synthesis of 1,4-disubstituted 3-methylidenedihydroquinolin-2(1H)-ones

被引：3

作者：

Pieta, Marlena ^{[1
]}

Kedzia, Jacek ^{[1
]}

Wojciechowski, Jakub ^{[2
]}

Janecki, Tomasz ^{[1
]}

机构：

[1] Lodz Univ Technol, Inst Organ Chem, Zeromskiego 116, PL-90924 Lodz, Poland

[2] Lodz Univ Technol, Inst Gen & Ecol Chem, Zeromskiego 116, PL-90924 Lodz, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 04期

关键词：

GAMMA-BUTYROLACTONES; DELTA-LACTONES; 3-METHYLIDENECHROMAN-2-ONES; REAGENTS;

D O I：

10.1016/j.tetasy.2017.03.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of enantiomerically pure or highly enriched (R)- or (S)-3-methylidenetetrahydroquinolin-2-ones was readily prepared by highly diastereoselective Michael additions of various Grignard reagents to quinolin-2(1H)-ones, containing an (R,R)- or (S,S)-di(1-phenylethylamino)phosphoryl group as chiral auxiliary, followed by Horner-Wadsworth-Emmons olefination of formaldehyde. An efficient synthesis of the starting (R,R)- and (S,S)-3-((di[(1-phenylethyl)amino]}phosphory1)-1-alkyl-quinolin-2(1H)-ones is also described. The relative and absolute configurations of the intermediate adducts and final methyli-denequinolinones were established by NMR and X-ray analysis. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：567 / 576

页数：10

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