Enantioselective Synthesis of Pyrroloindolines by a Formal [3+2] Cycloaddition Reaction

被引：180

作者：

Repka, Lindsay M. ^{[1
]}

Ni, Jane ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 41期

关键词：

STREPTOMYCES SP SUC1; BRONSTED ACID; CHIRAL DIOLS; ASYMMETRIC ALLYLBORATION; LEWIS-ACID; ALKALOIDS; CONSTRUCTION; STRATEGY; EXAMPLE; ENONES;

D O I：

10.1021/ja107328g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(R)-BINOL center dot SnCl4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.

引用

页码：14418 / 14420

页数：3

共 35 条

[1] Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid [J].

Angelini, Elena ;

Balsamini, Cesarino ;

Bartoccini, Francesca ;

Lucarini, Simone ;

Piersanti, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5654-5657

[2]

Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9

[3] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].

Austin, JF ;

Kim, SG ;

Sinz, CJ ;

Xiao, WJ ;

MacMillan, DWC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487

[4] PENTAVALENT ORGANOBISMUTH REAGENTS .2. THE PHENYLATION OF PHENOLS [J].

BARTON, DHR ;

BHATNAGAR, NY ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2657-2665

[5] CONFORMATIONAL-ANALYSIS OF SUBSTITUTED HEXAHYDROPYRROLO[2,3-B]INDOLES AND RELATED SYSTEMS - AN UNUSUAL EXAMPLE OF HINDERED ROTATION ABOUT SULFONAMIDE S-N BONDS - AN X-RAY CRYSTALLOGRAPHIC AND NMR-STUDY [J].

CRICH, D ;

BRUNCKO, M ;

NATARAJAN, S ;

TEO, BK ;

TOCHER, DA .

TETRAHEDRON, 1995, 51 (08) :2215-2228

[6] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis [J].

Crich, David ;

Banerjee, Abhisek .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) :151-161

[7]

Das B.C., 1974, TETRAHEDRON LETT, V15, P4299

[8] A simple method for the direct arylation of indoles [J].

Eastman, Kyle ;

Baran, Phil S. .

TETRAHEDRON, 2009, 65 (16) :3149-3154

[9] Cyclopropylazetoindolines as Precursors to C(3)-Quaternary-Substituted Indolines [J].

Espejo, Vinson R. ;

Li, Xi-Bo ;

Rainier, Jon D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8282-+

[10] Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress [J].

Isham, Crescent R. ;

Tibodeau, Jennifer D. ;

Jin, Wendy ;

Xu, Ruifang ;

Timm, Michael M. ;

Bible, Keith C. .

BLOOD, 2007, 109 (06) :2579-2588

← 1 2 3 4 →