Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

被引：39

作者：

Chai, Guo-Li ^{[1
]}

Sun, A-Qiang ^{[1
]}

Zhai, Dong ^{[2
]}

Wang, Juan ^{[1
]}

Deng, Wei-Qiao ^{[1
,2
]}

Wong, Henry N. C. ^{[1
,3
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Henan, Peoples R China

[2] Shandong Univ, Inst Mol Sci & Engn, Qingdao 266237, Shandong, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 13期

基金：

中国国家自然科学基金;

关键词：

ALKENYLBORONIC ACIDS; ALPHA; BETA-UNSATURATED KETONES; STEREOSELECTIVE-SYNTHESIS; 1,4-ADDITION REACTION; ALKYNYLATION; ARYL; TRIFLUOROMETHYLATION; ALKENYLATION; CONSTRUCTION; RATIONALE;

D O I：

10.1021/acs.orglett.9b01637

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-2,15-Br-2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to beta-trifluoromethyl alpha,beta-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.

引用

页码：5040 / 5045

页数：6

共 50 条

[31] Chiral ligand-controlled asymmetric conjugate addition of α-trimethylsilanylacetate to acyclic and cyclic enones
Iguchi, M
Doi, H
Hata, S
Tomioka, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (01) : 125 - 129
[32] Asymmetric Crossed-Conjugate Addition of Nitroalkenes to Enones by a Chiral Bifunctional Diamine Organocatalyst
Wang, Min
Lin, Lili
Shi, Jian
Liu, Xiaohua
Kuang, Yulong
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2365 - 2368
[33] Trifluoroacetic anhydride-catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones
Roscales, Silvia
Rincon, Angela
Buxaderas, Eduardo
Csaky, Aurelio G.
TETRAHEDRON LETTERS, 2012, 53 (35) : 4721 - 4724
[34] Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones
Holder, Jeffrey C.
Goodman, Emmett D.
Kikushima, Kotaro
Gatti, Michele
Marziale, Alexander N.
Stoltz, Brian M.
TETRAHEDRON, 2015, 71 (35) : 5781 - 5792
[35] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES
AHN, KH
KLASSEN, RB
LIPPARD, SJ
ORGANOMETALLICS, 1990, 9 (12) : 3178 - 3181
[36] Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite
Yan, M
Yang, LW
Wong, KY
Chan, ASC
CHEMICAL COMMUNICATIONS, 1999, (01) : 11 - 12
[37] Cu-catalyzed asymmetric conjugate addition to a variety of cyclic and acyclic enones.
Degrado, SJ
Mizutani, H
Hoveyda, AH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U209 - U210
[38] Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones
Gou, Shaohua
Ye, Zhongbin
Shi, Leiting
Qing, Dayong
Zhang, Wen
Wang, Yuliang
APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (07) : 517 - 522
[39] Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones
Yuan, Shuai
Zeng, Qingle
Wang, Jiajun
Zhou, Lihong
ARKIVOC, 2017, : 32 - 42
[40] Copper-Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands
Palais, Laetitia
Alexakis, Alexandre
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (40) : 10473 - 10485

← 1 2 3 4 5 →