Asymmetric Michael addition of 1,3-bis(phenylthio)propan-2-one to nitroalkenes employing Takemoto's thiourea catalyst

被引：7

作者：

Ansari, Samira ^{[1
]}

Raabe, Gerhard ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 05期

关键词：

Organocatalysis; Michael addition; Asymmetric synthesis; Thiourea; Nitroalkene; Ketones; CONJUGATE ADDITION; ALDEHYDES; KETONES; CARBON;

D O I：

10.1007/s00706-012-0915-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic direct asymmetric Michael addition of bis(phenylthio)propan-2-one to differently substituted aromatic nitroalkenes is described. Takemoto's thiourea catalyst efficiently promoted this reaction under mild conditions producing the desired products in synthetically useful yields and diastereo- and enantioselectivities. A single crystallization step could further improve the enantiomeric excess up to 98 %.

引用

页码：641 / 646

页数：6

共 62 条

[1] Influence of the Reaction Conditions on the Evolution of the Michael Addition of β-Keto Sulfones to α,β-Unsaturated Aldehydes [J].

Aleman, Jose ;

Marcos, Vanesa ;

Marzo, Leyre ;

Garcia Ruano, Jose Luis .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) :4482-4491

[2] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[3]

BARRETT AGM, 1988, TETRAHEDRON LETT, V29, P5735

[4] ALDOL AND MICHAEL ADDITIONS OF FLUORINATED NITROALKANES TO ALDEHYDES, KETONES, AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

BECK, AK ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1991, 124 (12) :2897-2911

[5] Organocatalytic Formation of Quaternary Stereocenters [J].

Bella, Marco ;

Gasperi, Tecla .

SYNTHESIS-STUTTGART, 2009, (10) :1583-1614

[6]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[7] A Simplified Synthesis of Takemoto's Catalyst [J].

Berkessel, A. ;

Seelig, B. .

SYNTHESIS-STUTTGART, 2009, (12) :2113-2115

[8] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[9] Enantioselective Catalytic α-Alkylation of Aldehydes via an SN1 Pathway [J].

Brown, Adam R. ;

Kuo, Wen-Hsin ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (27) :9286-9288

[10] The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].

Bur, SK ;

Padwa, A .

CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432

← 1 2 3 4 5 6 7 →