Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles

被引：172

作者：

Trost, Barry M. ^{[1
]}

Zhang, Yong ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 47期

关键词：

D O I：

10.1021/ja0755717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.

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页码：14548 / +

页数：3

相关论文

共 27 条

[1]

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

[2]

Belda O, 2002, SYNTHESIS-STUTTGART, P1601

[3] All-carbon quaternary stereogenic centers by enantioselective Cu-catalyzed conjugate additions promoted by a chiral N-heterocyclic carbene [J].

Brown, M. Kevin ;

May, Tricia L. ;

Baxter, Carl A. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1097-1100

[4] Surprises in enolate binding at high valent molybdenum [J].

Cameron, PA ;

Britovsek, GJP ;

Gibson, VC ;

Williams, DJ ;

White, AJP .

CHEMICAL COMMUNICATIONS, 1998, (07) :737-738

[5] Synthesis and aldol reactivity of O- and C-enolate complexes of nickel [J].

Cámpora, J ;

Maya, CM ;

Palma, P ;

Carmona, E ;

Gutiérrez-Puebla, E ;

Ruiz, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1482-1483

[6] Carbon-carbon bond-forming reductive elimination from arylpalladium complexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity [J].

Culkin, DA ;

Hartwig, JF .

ORGANOMETALLICS, 2004, 23 (14) :3398-3416

[7] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].

Douglas, CJ ;

Overman, LE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367

[8] Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via Cu-catalyzed conjugate addition of dialkylzinc reagents to 5-(1-arylalkylidene) Meldrum's acids [J].

Fillion, E ;

Wilsily, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2774-2775

[9] STRUCTURE AND REACTIONS OF OXAMETALLACYCLOBUTANES AND OXAMETALLACYCLOBUTENES OF RUTHENIUM [J].

HARTWIG, JF ;

BERGMAN, RG ;

ANDERSEN, RA .

ORGANOMETALLICS, 1991, 10 (09) :3344-3362

[10] SYNTHESIS OF (PME3)4RU(ME)(OC(CH2)ME) AS AN EQUILIBRIUM MIXTURE OF OXYGEN-BOUND AND CARBON-BOUND TRANSITION-METAL ENOLATES - THERMAL ELIMINATION OF METHANE TO FORM AN ETA-4-OXATRIMETHYLENEMETHANE COMPLEX [J].

HARTWIG, JF ;

ANDERSEN, RA ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5670-5671