Diastereoselective Mukaiyama aldol reaction of (N-alkyl) isatins with 2-(trimethylsilyloxy)furan by using lanthanum triflate

被引：22

作者：

Meshram, Harshadas Mitaram ^{[1
]}

Ramesh, Palakuri ^{[1
]}

Reddy, Bandi Chennakesava ^{[1
]}

Sridhar, Balasubramanian ^{[2
]}

Yadav, Jhillu Singh ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2011年 / 67卷 / 17期

关键词：

Mukaiyama aldol reaction; Isatins; 2-(trimethylsilyloxy)furan; La(OTf)(3); ENANTIOSELECTIVE TOTAL-SYNTHESIS; CATALYZED ASYMMETRIC ADDITION; SUBSTITUTED ISATINS; ARYLBORONIC ACIDS; ALDEHYDES; DERIVATIVES; ALPHA; 2-TRIMETHYLSILYLOXYFURAN; CONDENSATION; OXINDOLES;

D O I：

10.1016/j.tet.2011.02.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient vinylogous Mukaiyama aldol reaction (VMAR) of 2-(trimethylsilyloxy)furan with various (N-alkyl)isatins is described in the presence of lanthanum(III) triflates (5 mol %). The reaction proceeds rapidly and affords the corresponding 3-hydroxy-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-one in high yields with good diastereoselectivities (threo:erythro ratio up to <= 95:5). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3150 / 3155

页数：6

共 44 条

[31] Effective synthesis of 5-substituted butenolide derivatives by using cinchonidine-derived quaternary ammonium phenoxide catalyst [J].

Nagao, Hitoshi ;

Yamane, Yoshinobu ;

Mukaiyama, Teruaki .

CHEMISTRY LETTERS, 2007, 36 (01) :8-9

[32] N-heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds:: Stereoselective synthesis of spiro γ-butyrolactones [J].

Nair, V ;

Vellalath, S ;

Poonoth, M ;

Mohan, R ;

Suresh, E .

ORGANIC LETTERS, 2006, 8 (03) :507-509

[33] Enantioselective Synthesis of (R)-Convolutamydine A with New N-Heteroarylsulfonylprolinamides [J].

Nakamura, Shuichi ;

Hara, Noriyuki ;

Nakashima, Hiroki ;

Kubo, Koji ;

Shibata, Norio ;

Toru, Takeshi .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (27) :8079-8081

[34] Enantioselective total synthesis of convolutamydines B and E [J].

Nakamura, T ;

Shirokawa, S ;

Hosokawa, S ;

Nakazaki, A ;

Kobayashi, S .

ORGANIC LETTERS, 2006, 8 (04) :677-679

[35] Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system [J].

Palombi, Laura ;

Acocella, Maria R. ;

Celenta, Nicoletta ;

Massa, Antonio ;

Villano, Rosaria ;

Scettri, Arrigo .

TETRAHEDRON-ASYMMETRY, 2006, 17 (23) :3300-3303

[36] RECENT ADVANCES IN CHEMISTRY OF UNSATURATED LACTONES [J].

RAO, YS .

CHEMICAL REVIEWS, 1976, 76 (05) :625-694

[37] Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins [J].

Shintani, Ryo ;

Inoue, Mitsunori ;

Hayashi, Tamio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (20) :3353-3356

[38] Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products [J].

Suárez-Castillo, OR ;

Sánchez-Zavala, M ;

Meléndez-Rodríguez, M ;

Castelán-Duarte, LE ;

Morales-Ríos, MS ;

Joseph-Nathan, P .

TETRAHEDRON, 2006, 62 (13) :3040-3051

[39]

Szlosek M, 2000, ANGEW CHEM INT EDIT, V39, P1799, DOI 10.1002/(SICI)1521-3773(20000515)39:10<1799::AID-ANIE1799>3.0.CO

[40]

2-Z

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