Enantioselective 1,3-dipolar cycloadditions of diazoacetates with electron-deficient olefins

被引：97

作者：

Sibi, Mukund P. ^{[1
]}

Stanley, Levi M. ^{[1
]}

Soeta, Takahiro ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 08期

关键词：

D O I：

10.1021/ol070364x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to beta-substituted, alpha-substituted, and alpha,beta-disubstituted alpha,beta-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive alpha,beta-disubstituted dipolarophiles require elevated reaction temperatures, but still provide the corresponding pyrazolines with excellent enantioselectivities. Finally, an efficient synthesis of (-)-manzacidin A employing this cycloaddition methodology as a key step is illustrated.

引用

页码：1553 / 1556

页数：4

共 36 条

[1] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395

[2] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].

Chen, Wei ;

Yuan, Xiang-Hong ;

Li, Rui ;

Du, Wei ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822

[3] Enantioselective nitrone cycloadditions of α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-cerium(IV) triflate complexes [J].

Evans, David A. ;

Song, Hyun-Ji ;

Fandrick, Keith R. .

ORGANIC LETTERS, 2006, 8 (15) :3351-3354

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

Gothelf, KV ;

Jorgensen, KA .

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

[5] FRONTIER MOLECULAR-ORBITALS OF 1,3 DIPOLES AND DIPOLAROPHILES [J].

HOUK, KN ;

SIMS, J ;

DUKE, RE ;

STROZIER, RW ;

GEORGE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7287-7301

[6] ORIGIN OF REACTIVITY, REGIOSELECTIVITY, AND PERISELECTIVITY IN 1,3-DIPOLAR CYCLOADDITIONS [J].

HOUK, KN ;

SIMS, J ;

WATTS, CR ;

LUSKUS, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7301-7315

[7] Lewis acid-catalyzed enantioselective 1,3-dipolar cycloadditions of diazoalkane: Chiral ligand/achiral auxiliary cooperative chirality control [J].

Kanemasa, S ;

Kanai, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10710-10711

[8] Total synthesis of natural tert-alkylamino hydroxy carboxylic acids [J].

Kang, SH ;

Kang, SY ;

Lee, HS ;

Buglass, AJ .

CHEMICAL REVIEWS, 2005, 105 (12) :4537-4558

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

Kano, T ;

Hashimoto, T ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2174-2175

[10] Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral lewis acid [J].

Kano, T ;

Hashimoto, T ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11926-11927

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