Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr2 as promoter via a one-pot three-component reaction

被引：23

作者：

Wei, HX ^{[1
]}

Jasoni, RL ^{[1
]}

Hu, JL ^{[1
]}

Li, GG ^{[1
]}

Paré, PW ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 45期

关键词：

Baylis-Hillman adducts; magnesium bromine; alpha; beta-acetylenic ketones; (Z)-beta-bromovinyl ketone;

D O I：

10.1016/j.tet.2004.08.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first time steroselective synthesis of (Z)-beta-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with alpha,beta-acetylenic ketones to form an active beta-bromo allenolate intermediate, which in turn attacks various aldehydes to afford beta-bromo Baylis-Hillman adducts in good yields and Z-selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：10233 / 10237

页数：5

共 50 条

[21] L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones
Dodda, Rajasekhar
Zhao, Cong-Gui
SYNTHESIS-STUTTGART, 2006, 19 (19): : 3238 - 3242
[22] The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes
Basavaiah, D
Sharada, DS
Kumaragurubaran, N
Reddy, RM
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7135 - 7137
[23] Stereoselective Synthesis of Phenyl-1,2,3-triazoles Containing (E)-Vinyl Halide Group via a One-Pot, Three-Component Reaction
Zhang, Wensheng
Su, Changhui
Kuang, Chunxiang
Yang, Qing
SYNTHETIC COMMUNICATIONS, 2011, 41 (09) : 1267 - 1275
[24] Stereoselective, One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyrans from Epoxides via Prins Cyclization Reaction
Indukuri, Kiran
Bondalapati, Somasekhar
Kotipalli, Trimurtulu
Gogoi, Paramartha
Saikia, Anil K.
SYNLETT, 2012, (02) : 233 - 238
[25] Stereoselective One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyran via Prins-Friedel-Crafts Reaction
Reddy, U. C.
Bondalapati, S.
Saikia, Anil K.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06): : 2605 - 2608
[26] First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives
Basavaiah, D
Rao, AJ
CHEMICAL COMMUNICATIONS, 2003, (05) : 604 - 605
[27] Nanostructured Zirconium Pyrophosphate Catalyzed Diastereoselective Synthesis of β-Amino Ketones via One-Pot Three-Component Mannich Reaction
Houda Maati
Othmane Amadine
Younes Essamlali
Aziz Fihri
Abdallah Rhihil
Christophe Len
Mohamed Zahouily
Catalysis Letters, 2018, 148 : 699 - 711
[28] Nanostructured Zirconium Pyrophosphate Catalyzed Diastereoselective Synthesis of β-Amino Ketones via One-Pot Three-Component Mannich Reaction
Maati, Houda
Amadine, Othmane
Essamlali, Younes
Fihri, Aziz
Rhihil, Abdallah
Len, Christophe
Zahouily, Mohamed
CATALYSIS LETTERS, 2018, 148 (02) : 699 - 711
[29] A facile method for the synthesis of nicotinonitriles from ketones via a one-pot chloromethyleneiminium salt mediated three-component reaction
Asokan, C. V.
Anabha, E. R.
Thomas, Ajith Dain
Jose, Ann Maria
Lethesh, K. C.
Prasanth, M.
Krishanraj, K. U.
TETRAHEDRON LETTERS, 2007, 48 (32) : 5641 - 5643
[30] Palladium-Catalyzed Three-Component Tandem Reaction for One-pot Highly Stereoselective Synthesis of (Z)-α-Hydroxymethyl Allylic Sulfones
Hou, Yunlei
Shen, Qi
Li, Zefei
Chen, Shaowei
Zhao, Yanfang
Qin, Mingze
Gong, Ping
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 631 - 636

← 1 2 3 4 5 →