Highly Chemo-, Enantio-, and Regioselective Synthesis of α,α-Disubstituted Furanones by Cu-Catalyzed Conjugate Addition

被引：17

作者：

Endo, Kohei ^{[1
,2
]}

Yakeishi, Sayuri ^{[3
]}

Takayama, Ryotaro ^{[3
]}

Shibata, Takanori ^{[3
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Dept Chem, Kanazawa, Ishikawa 9201192, Japan

[2] PRESTO Japan Sci & Technol Agcy JST, Kawaguchi, Saitama 3320012, Japan

[3] Waseda Univ, Grad Sch Sci & Technol, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 29期

关键词：

addition reactions; aluminum; asymmetric synthesis; copper; heterocyclic compounds; QUATERNARY STEREOGENIC CENTERS; SUBSTITUTED CYCLIC ENONES; ENANTIOSELECTIVE ALPHA-ARYLATION; ASYMMETRIC ALLYLIC ALKYLATION; ARYL ALUMINUM REAGENTS; TRISUBSTITUTED ENONES; ORGANOZINC REAGENTS; GRIGNARD-REAGENTS; CHIRAL CENTERS; MONO-PHOS;

D O I：

10.1002/chem.201403446

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an alpha,alpha- disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center.

引用

页码：8893 / 8897

页数：5

共 50 条

[41] An enantioselective catalytic approach to syn deoxypropionate units combining asymmetric Cu-catalyzed 1,6-and 1,4-conjugate addition
den Hartog, Tim
van Dijken, Derk Jan
Minnaard, Adriaan J.
Feringa, Ben L.
TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1574 - 1584
[42] Highly Enantio- and Diastereoselective Synthesis of 1,2,3-Trisubstituted Cyclopropanes from α,β-Unsaturated Amides and Stabilized Sulfur Ylides Catalyzed by a Chiral Copper(I) Complex
Pagire, Santosh K.
Kumagai, Naoya
Shibasaki, Masakatsu
ACS CATALYSIS, 2021, 11 (18) : 11597 - 11606
[43] Metal-Free, Mild, Nonepimerizing, Chemo- and Enantio- or Diastereoselective N-Alkylation of Amines by Alcohols via Oxidation/Imine-Iminium Formation/Reductive Amination: A Pragmatic Synthesis of Octahydropyrazinopyridoindoles and Higher Ring Analogues
Khan, Imran A.
Saxena, Anil K.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) : 11656 - 11669
[44] Highly Diastereo- and Enantioselective Synthesis of Chiral Cyclohexylphosphines by Cu-Catalyzed Phosphination-Aldol Cyclization of Ketone-Enamides
Li, Junbao
Sun, Jinghui
Yan, Yifei
Dong, Zhuyong
Xu, Jun
Li, Wanmei
Huang, Yinhua
ORGANIC LETTERS, 2023, 26 (01) : 210 - 214
[45] Stereoselective synthesis of exocyclic alkenes by Cu-catalyzed allylmagnesiation, Pd-catalyzed alkylation, and Ru-catalyzed ring-closing metathesis:: Highly stereoselective synthesis of (Z)- and (E)-γ-bisabolenes
Anastasia, L
Dumond, YR
Negishi, E
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (16) : 3039 - 3043
[46] Synthesis of novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions
Xia, Haijun
Yan, Hua
Shen, Chao
Shen, Fangyi
Zhang, Pengfei
CATALYSIS COMMUNICATIONS, 2011, 16 (01) : 155 - 158
[47] Cu-Catalyzed Selective Synthesis of Propargylamines via A3-Coupling/Aza-Michael Addition Sequence: Amine Loading Controls the Selectivity
Feng, Huangdi
Peng, Futao
Xi, Hui
Zhong, Ling
Huang, Liliang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 762 - 765
[48] Monodentate Non-C2-symmetric Chiral N-Heterocyclic Carbene Complexes for Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and Alkenylsilylfluorides to Cyclic Enones
Lee, Kang-Sang
Hoveyda, Amir H.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4455 - 4462
[49] Chiral, Chelating, Hydroxyalkyl and Hydroxyaryl N-Heterocyclic Carbenes: Design, Synthesis, and Application in Copper-Catalyzed Asymmetric Conjugate Addition (Cu-ACA)
Wencel, Joanna
Mouduit, Marc
Henon, Helene
Kehrli, Stefan
Alexakis, Alexandre
ALDRICHIMICA ACTA, 2009, 42 (02) : 43 - 50
[50] Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones
Malapit, Christian A.
Luvaga, Irungu K.
Caldwell, Donald R.
Schipper, Nicholas K.
Howell, Amy R.
ORGANIC LETTERS, 2017, 19 (17) : 4460 - 4463

← 1 2 3 4 5 →