Unusually Reactive and Selective Carbonyl Ylides for Three-Component Cycloaddition Reactions

被引：83

作者：

DeAngelis, Andrew ^{[1
]}

Taylor, Michael T. ^{[1
]}

Fox, Joseph M. ^{[1
]}

机构：

[1] Univ Delaware, Brown Labs, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 03期

关键词：

1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; AZOMETHINE YLIDES; ALPHA-DIAZOESTERS; ALDEHYDES; CYCLIZATION; DIOXOLANES; DICARBOMETHOXYCARBENE; CARBENOIDS;

D O I：

10.1021/ja807184r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conditions are described for the Rh-catalyzed formation of highly functionalized dihydro- and tetrahydrofuran products via three-component reactions of alclehydes, alpha-alkyl-alpha-diazoesters, and dipolarophiles. The alkyl-substituted carbonyl ylides that are generated in this fashion are highly reactive in cycloaddition reactions and display a scope of reactivity that is much broader than the three-component reactions of carbonyl ylides derived from ethyl diazoacetate or alpha-aryl-alpha-diazoesters. The reactions of alkyl-substituted carbonyl ylides proceed with high regioselectivity and diastereoselectivity that are rationalized in terms of an asynchronous, endo-selective transition state.

引用

页码：1101 / 1105

页数：5

共 39 条

[21] Highly enantio- and diastereoselective construction of 1,2-disubstituted cyclopentane compounds by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]-catalyzed C-H insertion reactions of α-diazo esters [J].

Minami, K ;

Saito, H ;

Tsutsui, H ;

Nambu, H ;

Anada, M ;

Hashimoto, S .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1483-1487

[22] Regioselective synthesis of mono- and bis-decahydrobenzocarbazoles via tandem reactions of α-diazo ketones [J].

Muthusamy, S ;

Gunanathan, C ;

Suresh, E .

TETRAHEDRON, 2004, 60 (36) :7885-7897

[23] Multicomponent reactions of diazoamides: Diastereoselective synthesis of mono- and bis-spirofurooxindoles [J].

Muthusamy, S ;

Gunanathan, C ;

Nethaji, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5631-5637

[24] A stereoselective synthesis of spiro-dioxolanes via the multicomponent reaction of dicarbomethoxycarbene, aldehydes and 1,2-or 1,4-diones [J].

Nair, V ;

Mathai, S ;

Mathew, SC ;

Rath, NP .

TETRAHEDRON, 2005, 61 (11) :2849-2856

[25] The three-component reaction of dicarbomethoxycarbene, aldehydes, and β-nitrostyrenes:: A stereoselective synthesis of substituted tetrahydrofurans [J].

Nair, V ;

Mathai, S ;

Varma, RL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1413-1414

[26] A facile three-component reaction of dicarbomethoxycarbene, aldehydes and o-quinones:: synthesis of novel spiro-dioxolanes [J].

Nair, V ;

Mathai, S ;

Nair, SM ;

Rath, NP .

TETRAHEDRON LETTERS, 2003, 44 (46) :8407-8409

[27] SYNTHESIS OF FUNCTIONALIZED AZOMETHINE YLIDES VIA THE RH(II)-CATALYZED CYCLIZATION OF ALPHA-DIAZO CARBONYLS ONTO IMINO PI-BONDS [J].

PADWA, A ;

DEAN, DC ;

OSTERHOUT, MH ;

PRECEDO, L ;

SEMONES, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5347-5357

[28] YLIDE FORMATION FROM THE REACTION OF CARBENES AND CARBENOIDS WITH HETEROATOM LONE PAIRS [J].

PADWA, A ;

HORNBUCKLE, SF .

CHEMICAL REVIEWS, 1991, 91 (03) :263-309

[29] Model studies directed toward the total synthesis of (±)-ribasine.: A tandem cyclization-cycloaddition route leading to the core skeleton [J].

Padwa, A ;

Precedo, L ;

Semones, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :4079-4088

[30] Rh-catalyzed intermolecular cyclopropanation with α-alkyl-α-diazoesters:: Catalyst-dependent chemo- and diastereoselectivity [J].

Panne, Patricia ;

DeAngelis, Andrew ;

Fox, Joseph M. .

ORGANIC LETTERS, 2008, 10 (14) :2987-2989

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