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.

引用

页码：14548 / +

页数：3

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
Brown, M. Kevin
May, Tricia L.
Baxter, Carl A.
Hoveyda, Amir H.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) : 1097 - 1100
[4] Surprises in enolate binding at high valent molybdenum
Cameron, PA
Britovsek, GJP
Gibson, VC
Williams, DJ
White, AJP
[J]. CHEMICAL COMMUNICATIONS, 1998, (07) : 737 - 738
[5] Synthesis and aldol reactivity of O- and C-enolate complexes of nickel
Cámpora, J
Maya, CM
Palma, P
Carmona, E
Gutiérrez-Puebla, E
Ruiz, C
[J]. 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
Culkin, DA
Hartwig, JF
[J]. ORGANOMETALLICS, 2004, 23 (14) : 3398 - 3416
[7] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
Douglas, CJ
Overman, LE
[J]. 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
Fillion, E
Wilsily, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) : 2774 - 2775
[9] STRUCTURE AND REACTIONS OF OXAMETALLACYCLOBUTANES AND OXAMETALLACYCLOBUTENES OF RUTHENIUM
HARTWIG, JF
BERGMAN, RG
ANDERSEN, RA
[J]. 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
HARTWIG, JF
ANDERSEN, RA
BERGMAN, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) : 5670 - 5671

← 1 2 3 →