Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols

被引：67

作者：

Bishop, Joshua A. ^{[1
]}

Lou, Sha ^{[1
]}

Schaus, Scott E. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 24期

关键词：

enantioselectivity; boronates; homogeneous catalysis; synthetic methods; natural products; ELECTROSPRAY MASS-SPECTROMETRY; DIASTEREOSELECTIVE ADDITION; ASYMMETRIC ALLYLBORATION; ORGANOMETALLIC REAGENTS; LIGANDS; LIBRARY; AMINES; IDENTIFICATION; OPTIMIZATION; DISCOVERY;

D O I：

10.1002/anie.200901023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On the big screen: A chiral biphenol catalyst screening protocol was developed for the rapid identification of enantioselective nucleophilic boronate reactions with acyl imines (see scheme). The approach successfully identified a unique catalyst for the reaction of aryl, vinyl, and alkynyl boronates. Mechanistic studies demonstrate boronate ligand exchange with the catalyst is necessary for activation towards nucleophilic addition. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4337 / 4340

页数：4

共 48 条

[1] Synthesis and applications of chiral organoboranes generated from sulfonium ylides [J].

Aggarwal, VK ;

Fang, GY ;

Schmidt, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) :1642-1643

[2] Diastereoselective addition of allylmetal compounds to imines derived from (S)-1-phenylethanamine [J].

Alvaro, G ;

Boga, C ;

Savoia, D ;

UmaniRonchi, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (09) :875-882

[3] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].

Bolshan, Y ;

Batey, RA .

ORGANIC LETTERS, 2005, 7 (08) :1481-1484

[4] BINOL: A versatile chiral reagent [J].

Brunel, JM .

CHEMICAL REVIEWS, 2005, 105 (03) :857-897

[5] Practical implications of some recent studies in electrospray ionization fundamentals [J].

Cech, NB ;

Enke, CG .

MASS SPECTROMETRY REVIEWS, 2001, 20 (06) :362-387

[6] Modified BINOL ligands in asymmetric catalysis [J].

Chen, Y ;

Yekta, S ;

Yudin, AK .

CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211

[7]

Cole R.B., 1997, ELECTROSPRAY IONIZAT

[8] Electrospray mass spectrometry applied inorganic and organometallic chemistry [J].

Colton, R ;

DAgostino, A ;

Traeger, JC .

MASS SPECTROMETRY REVIEWS, 1995, 14 (02) :79-106

[9] Catalytic enantioselective indium-mediated allylation of hydrazones [J].

Cook, GR ;

Kargbo, R ;

Maity, B .

ORGANIC LETTERS, 2005, 7 (13) :2767-2770

[10] Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope [J].

Copeland, GT ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6496-6502

← 1 2 3 4 5 →