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

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