Au(I)-catalyzed enantioselective 1,3-dipolar cycloadditions of Munchnones with electron-deficient Alkenes

被引：161

作者：

Melhado, Asa D. ^{[1
]}

Luparia, Marco ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 42期

关键词：

D O I：

10.1021/ja074824t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first catalytic enantioselective 1,3-dipolar cycloaddition of munchnone dipoles with electron -deficent alkenes is described. The reaction is catalyzed by chiral bis(phosphine)gold(I) benzoate complexes and provides Delta(1)-pyrrolines with excellent regio-, diastereo-, and enantioselectivity. The reaction is proposed to proceed through a 1,3-dipole generated by deprotonation of a gold(I)activated azlactone.

引用

页码：12638 / +

页数：3

共 35 条

[1] AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].

Asao, N ;

Aikawa, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459

[2] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[3] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[4] AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].

Asao, N ;

Sato, K ;

Menggenbateer ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685

[5] Lewis acid-catalyzed [4+2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives [J].

Asao, Naoki ;

Aikawa, Haruo .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5249-5253

[6] 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

[7] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].

Chen, C ;

Li, XD ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175

[8] Palladium-catalyzed multicomponent coupling of alkynes, imines, and acid chlorides: A direct and modular approach to pyrrole synthesis [J].

Dhawan, R ;

Arndtsen, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :468-469

[9] The development of a catalytic synthesis of Munchnones:: A simple four-component coupling approach to α-amino acid derivatives [J].

Dhawan, R ;

Dghaym, RD ;

Arndtsen, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1474-1475

[10]

FURSTNER A, 2007, ANGEW CHEM INT EDIT, V46, P2

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