Catalytic asymmetric conjugate addition of Grignard reagents to chromones

被引：49

作者：

Vila, Carlos ^{[1
]}

Hornillos, Valentin ^{[1
]}

Fananas-Mastral, Martin ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 53期

关键词：

PHOSPHINE-PHOSPHITE LIGANDS; 2-SUBSTITUTED CHROMAN-4-ONES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; CHROMANONES; COMPLEXES; ENONES; 1,4-ADDITION; CONSTRUCTION; FLAVANONES;

D O I：

10.1039/c3cc43105c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regio- and enantioselective copper catalysed direct conjugate addition of Grignard reagents to chromones has been developed taking advantage of the reduced reactivity of the resulting magnesium enolates. This methodology tolerates a broad scope of alkyl Grignards including secondary alkyl magnesium reagents as well as functionalised chromones.

引用

下载

页码：5933 / 5935

页数：3

共 50 条

[1] Catalytic asymmetric conjugate addition of Grignard reagents
Feringa, BL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3172 - U3172
[2] Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents
Harutyunyan, Syuzanna R.
den Hartog, Tim
Geurts, Koen
Minnaard, Adriaan J.
Feringa, Ben L.
CHEMICAL REVIEWS, 2008, 108 (08) : 2824 - 2852
[3] Catalytic asymmetric conjugate addition of grignard reagents to (α,β-unsaturated sulfones
Bos, Pieter H.
Minnaard, Adriaan J.
Feringa, Ben L.
ORGANIC LETTERS, 2008, 10 (19) : 4219 - 4222
[4] Asymmetric Conjugate Addition of Grignard Reagents to Pyranones
Mao, Bin
Fananas-Mastral, Martin
Feringa, Ben L.
ORGANIC LETTERS, 2013, 15 (02) : 286 - 289
[5] Catalytic enantioselective conjugate addition with Grignard reagents
Lopez, Fernando
Minnaard, Adriaan J.
Feringa, Ben L.
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (03) : 179 - 188
[6] Asymmetric Catalytic Conjugate Addition of Cyanide to Chromones and β-Substituted Cyclohexenones
Mo, Yuhao
Chen, Qiyou
Li, Jinzhao
Ye, Dong
Zhou, Yuqiao
Dong, Shunxi
Liu, Xiaohua
Feng, Xiaoming
ACS CATALYSIS, 2023, 13 (02) : 877 - 886
[7] An iterative catalytic route to enantiopure deoxypropionate subunits:: Asymmetric conjugate addition of Grignard reagents to α,β-unsaturated thioesters
Mazery, RD
Pullez, M
López, F
Harutyunyan, SR
Minnaard, AJ
Feringa, BL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9966 - 9967
[8] Catalytic asymmetric conjugate addition of Grignard reagents to coumarins-synthesis of versatile chiral building blocks
Teichert, Johannes F.
Feringa, Ben L.
CHEMICAL COMMUNICATIONS, 2011, 47 (09) : 2679 - 2681
[9] CATALYTIC ASYMMETRIC CONJUGATE ADDITION OF GRIGNARD-REAGENTS MEDIATED BY COPPER(I)-CHIRAL BIDENTATE PHOSPHINE COMPLEX
KANAI, M
TOMIOKA, K
TETRAHEDRON LETTERS, 1995, 36 (24) : 4275 - 4278
[10] Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones
Feringa, BL
Badorrey, R
Peña, D
Harutyunyan, SR
Minnaard, AJ
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5834 - 5838

← 1 2 3 4 5 →