Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and α-substituted acroleins:: Total synthesis of manzacidin A

被引：158

作者：

Kano, T ^{[1
]}

Hashimoto, T ^{[1
]}

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 07期

关键词：

D O I：

10.1021/ja056851u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A titanium BINOLate catalyzed asymmetric 1,3-dipolar cycloaddition reaction between α-substituted acroleins and alkyl diazoacetates has been developed. With this methodology in hand, chiral 2-pyrazolines containing a quaternary stereogenic center were obtained in high to excellent enantioselectivities (up to 95% ee). The synthetic utility of the optically enriched 2-pyrazoline thus obtained was demonstrated in the short synthesis of manzacidin A. Copyright © 2006 American Chemical Society.

引用

页码：2174 / 2175

页数：2

共 37 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] BINOL: A versatile chiral reagent [J].

Brunel, JM .

CHEMICAL REVIEWS, 2005, 105 (03) :857-897

[4] Total synthesis of (±)-manzacidin D [J].

Drouin, C ;

Woo, JCS ;

MacKay, B ;

Lavigne, RMA .

TETRAHEDRON LETTERS, 2004, 45 (39) :7197-7199

[5] Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: An investigation on the synthesis of 3-hydroxy-2-arylacrylic acid ethyl esters [J].

Dudley, ME ;

Morshed, MM ;

Brennan, CL ;

Islam, MS ;

Ahmad, MS ;

Atuu, MR ;

Branstetter, B ;

Hossain, MM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7599-7608

[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] Catalytic asymmetric allylation of aldehydes and related reactions with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid [J].

Hanawa, H ;

Uraguchi, D ;

Konishi, S ;

Hashimoto, T ;

Maruoka, K .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) :4405-4413

[9] Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid:: Application to catalytic asymmetric allylation of aldehydes [J].

Hanawa, H ;

Hashimoto, T ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1708-1709

[10] 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

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