Catalytic enantioselective 1,3-dipolar cycloadditions of alkyl diazoacetates with α,β-disubstituted acroleins

被引：67

作者：

Gao, Lizhu ^{[1
]}

Hwang, Geum-Sook ^{[2
,3
]}

Lee, Mi Young ^{[1
]}

Ryu, Do Hyun ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Chungnam Natl Univ, Korea Basic Sci Inst, Seoul 136713, South Korea

[3] Chungnam Natl Univ, Grad Sch Analyt Sci & Technol, Seoul 136713, South Korea

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 36期

关键词：

DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; ACID; ALDEHYDES; CYANOSILYLATION; DIAZOMETHANE; KETONES; ESTERS;

D O I：

10.1039/b910321j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic route to highly functionalized chiral 2-pyrazolines by an asymmetric 1,3-dipolar cycloaddition reaction of ethyl diazoacetate with alpha-substituted and alpha,beta-disubstituted acroleins has been developed; in the presence of chiral (S)-oxazaborolidinium ion 1 as catalyst, the reaction proceeded with high to excellent enantioselectivities (up to 99% ee).

引用

页码：5460 / 5462

页数：3

共 30 条

[1]

Barluenga J, 1999, CHEM-EUR J, V5, P883, DOI 10.1002/(SICI)1521-3765(19990301)5:3<883::AID-CHEM883>3.0.CO

[2]

2-0

[3] Enantioselective Catalysis Based on Cationic Oxazaborolidines [J].

Corey, E. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2100-2117

[4] The formyl C-H•••O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydes [J].

Corey, EJ ;

Lee, TW .

CHEMICAL COMMUNICATIONS, 2001, (15) :1321-1329

[5] Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine [J].

Corey, EJ ;

Shibata, T ;

Lee, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3808-3809

[6] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[7] Versatile, diastereoselective additions of silyl ketene acetals, allyl tributylstannane, and Me3SiCN to N-acyl pyrazolines:: Asymmetric synthesis of densely functionalized pyrazolidines [J].

Guerra, FM ;

Mish, MR ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (26) :4265-4267

[8] Syntheses of manzacidins: a stage for the demonstration of synthetic methodologies [J].

Hashimoto, Takuya ;

Maruoka, Keiji .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (05) :829-835

[9] A SELECTIVE METHOD FOR THE DIRECT CONVERSION OF ALDEHYDES INTO BETA-KETO-ESTERS WITH ETHYL DIAZOACETATE CATALYZED BY TIN(II) CHLORIDE [J].

HOLMQUIST, CR ;

ROSKAMP, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3258-3260

[10] Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways [J].

Hu, QY ;

Zhou, G ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13708-13713

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