Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids

被引：29

作者：

Zhong, Fangrui ^{[1
,2
]}

Jiang, Chunhui ^{[1
,2
]}

Yao, Weijun ^{[1
,2
]}

Xu, Li-Wen ^{[3
]}

Lu, Yixin ^{[1
,2
]}

机构：

[1] Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117543, Singapore

[2] Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117543, Singapore

[3] Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 32期

关键词：

Molecular sieves; Decarboxylation; Mannich reaction; Aldol reaction; Ketoacids; ACID HALF-THIOESTERS; ASYMMETRIC-SYNTHESIS; ALLYLIC ALKYLATION; KETO ACIDS; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY STEREOCENTERS; POLYKETIDE SYNTHASES; PHOSPHINES SYNTHESIS; UNACTIVATED KETONES; MICHAEL-ADDITION;

D O I：

10.1016/j.tetlet.2013.06.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A molecular sieve mediated decarboxylative Mannich reaction of beta-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful beta-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between beta-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4333 / 4336

页数：4

共 64 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2]

Albrecht S., 2011, ORG PROCESS RES DEV, V15, P503, DOI DOI 10.1021/0P2000207

[3] Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins [J].

Allu, Suresh ;

Molleti, Nagaraju ;

Panem, Ramachandrarao ;

Singh, Vinod K. .

TETRAHEDRON LETTERS, 2011, 52 (32) :4080-4083

[4]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[5]

2-E

[6] Organocatalytic Enantioselective Michael-Addition of Malonic Acid Half-Thioesters to β-Nitroolefins: From Mimicry of Polyketide Synthases to Scalable Synthesis of γ-Amino Acids [J].

Bae, Han Yong ;

Some, Surajit ;

Lee, Jae Heon ;

Kim, Ju-Young ;

Song, Myoung Jong ;

Lee, Sungyul ;

Zhang, Yong Jian ;

Song, Choong Eui .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) :3196-3202

[7]

Baktharaman S, 2008, ALDRICHIM ACTA, V41, P109

[8] Strategies for the enantioselective synthesis of spirooxindoles [J].

Ball-Jones, Nicolas R. ;

Badillo, Joseph J. ;

Franz, Annaliese K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181

[9] Environmentally benign metal-free decarboxylative aldol and Mannich reactions [J].

Baudoux, Jerome ;

Lefebvre, Pierre ;

Legay, Remi ;

Lasne, Marie-Claire ;

Rouden, Jacques .

GREEN CHEMISTRY, 2010, 12 (02) :252-259

[10] Asymmetric Malonic and Acetoacetic Acid Syntheses - A Century of Enantioselective Decarboxylative Protonations [J].

Blanchet, Jerome ;

Baudoux, Jerome ;

Amere, Mukkanti ;

Lasne, Marie-Claire ;

Rouden, Jacques .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (33) :5493-5506

← 1 2 3 4 5 6 7 →