Stereocontrolled Creation of All-Carbon Quaternary Stereocenters by Organocatalytic Conjugate Addition of Oxindoles to Vinyl Sulfone

被引：145

作者：

Zhu, Qiang ^{[1
]}

Lu, Yixin ^{[1
,2
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[2] Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117548, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 42期

关键词：

amino acids; asymmetric synthesis; conjugate addition; multifunctional catalysts; oxindoles; ASYMMETRIC MICHAEL ADDITION; SELECTIVE MANNICH REACTIONS; ENANTIOSELECTIVE FLUORINATION; CATALYSTS; ALDEHYDES; NITROALKENES; MALONATE; HYDROXYLATION; CONSTRUCTION; TRYPTOPHAN;

D O I：

10.1002/anie.201003837

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Multifunctional catalysts in operation: A novel class of trifunctional thiourea catalysts containing natural amino acid residues have been prepared (see scheme), and found to be very effective towards the asymmetric addition of 3-alkyl-oxindoles to 1,1-bis(benzenesulfonyl)ethylene. This synthetic protocol has led to the enantioselective synthesis of 3-alkyl-3-aryl-disubstituted oxindoles and indolines with an all-carbon quaternary stereogenic center. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7753 / 7756

页数：4

共 99 条

[1] Enantioselective Organocatalytic Addition of Oxazolones to 1,1-Bis(phenylsulfonyl)ethylene: A Convenient Asymmetric Synthesis of Quaternary α-Amino Acids [J].

Alba, Andrea-Nekane R. ;

Companyo, Xavier ;

Valero, Guillem ;

Moyano, Albert ;

Rios, Ramon .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5354-5361

[2] Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters [J].

Aleman, Jose ;

Reyes, Efraim ;

Richter, Bo ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2007, (38) :3921-3923

[3]

[Anonymous], 2010, ANGEW CHEM

[4]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[5]

[Anonymous], 2006, ANGEW CHEM

[6]

[Anonymous], ANGEW CHEM

[7] A novel organocatalytic tool for the iminium activation of α,β-unsaturated ketones [J].

Bartoli, Giuseppe ;

Melchiorre, Paolo .

SYNLETT, 2008, (12) :1759-1772

[8] CC-1065 and the duocarmycins: Synthetic studies [J].

Boger, DL ;

Boyce, CW ;

Garbaccio, RM ;

Goldberg, JA .

CHEMICAL REVIEWS, 1997, 97 (03) :787-828

[9]

Brown R. T., 1983, CHEM HETEROCYCLIC 4, V25, P85

[10] Dimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives [J].

Bui, Tommy ;

Candeias, Nuno R. ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) :5574-+

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