Enantioselective Phase-Transfer Catalysis: Synthesis of Pyrazolines

被引：74

作者：

Mahe, Olivier ^{[1
,2
]}

Dez, Isabelle ^{[3
]}

Levacher, Vincent ^{[1
,2
]}

Briere, Jean-Francois ^{[1
,2
]}

机构：

[1] INSA, CNRS UMR COBRA, F-76131 Mont St Aignan, France

[2] Univ Rouen, FR 3038, IRCOF, F-76131 Mont St Aignan, France

[3] ENSICaen Univ Caen, CNRS, FR3038,Lab Chim Mol & Thioorgan, Caen, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 39期

关键词：

asymmetric synthesis; heterocycles; Michael addition; organocatalysis; phase-transfer catalysis; AZA-MICHAEL REACTIONS; ASYMMETRIC-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; CONJUGATE ADDITION; NITRILE IMINES; DERIVATIVES; DIAZOACETATES; OLEFINS; KETONES; SALTS;

D O I：

10.1002/anie.201002485

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

All paired up: Under catalytic phase-transfer conditions the formation of a chiral ion pair between quininium cation 1 and hydrazine anion 2 led to an enantioselective aza-Michael cyclocondensation domino reaction to furnish pyrazolines. A convenient one-pot protocol allowed exchange of the functional group (R1) on the nitrogen atom. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7072 / 7075

页数：4

共 50 条

[1] Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis
Trubitson, Dmitri
Martonova, Jevgenija
Erkman, Kristin
Metsala, Andrus
Saame, Jaan
Koster, Kristjan
Jarving, Ivar
Leito, Ivo
Kanger, Tonis
SYNTHESIS-STUTTGART, 2020, 52 (07): : 1047 - 1059
[2] Chemodivergent Preparation of Various Heterocycles via Phase-Transfer Catalysis: Enantioselective Synthesis of Functionalized Piperidines
Bertuzzi, Giulio
Silvestrini, Filippo
Moimare, Pierluigi
Pecorari, Daniel
Mazzanti, Andrea
Bernardi, Luca
Fochi, Mariafrancesca
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (05) : 1167 - 1175
[3] Enantioselective S-Alkylation of Sulfenamides by Phase-Transfer Catalysis
Champlin, Andrew T.
Kwon, Na Yeon
Ellman, Jonathan A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (42)
[4] Organocatalytic Enantioselective Synthesis of Pyrazolidines, Pyrazolines and Pyrazolidinones
Fernandez, Maitane
Reyes, Efraim
Vicario, Jose L.
Badia, Dolores
Carrillo, Luisa
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) : 371 - 376
[5] Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis
Duan, Shaobo
Li, Sanliang
Ye, Xinyi
Du, Nuan-Nuan
Tan, Choon-Hong
Jiang, Zhiyong
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) : 7770 - 7778
[6] Enantioselective α-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
Park, Cheonhyoung
Ha, Min Woo
Kim, Byungsoo
Hong, Suckchang
Kim, Doyoung
Park, Yohan
Kim, Mi-hyun
Lee, Jae Kyun
Lee, Jeeyeon
Park, Hyeung-geun
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (13) : 2841 - 2848
[7] Enantioselective synthesis of α-amino acids by chiral phase-transfer catalysis
Ooi, T
Maruoka, K
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (12) : 1195 - 1206
[8] Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis
Biswas, Souvagya
Kubota, Koji
Orlandi, Manuel
Turberg, Mathias
Miles, Dillon H.
Sigman, Matthew S.
Toste, F. Dean
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (02) : 589 - 593
[9] Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters
Lygo, Barry
Beynon, Christopher
McLeod, Michael C.
Roy, Claude-Eric
Wade, Charles E.
TETRAHEDRON, 2010, 66 (46) : 8832 - 8836
[10] Construction of Isoxazolidin-5-ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase-Transfer Catalysis
Cadart, Timothee
Levacher, Vincent
Perrio, Stephane
Briere, Jean-Francois
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1499 - 1509

← 1 2 3 4 5 →