Palladium-Catalyzed Intermolecular Aminocarbonylation of Alkenes: Efficient Access of β-Amino Acid Derivatives

被引：121

作者：

Cheng, Jiashun ^{[1
]}

Qi, Xiaoxu ^{[1
]}

Li, Ming ^{[1
]}

Chen, Pinhong ^{[1
]}

Liu, Guosheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 07期

关键词：

AEROBIC OXIDATIVE AMINATION; AZA-WACKER REACTIONS; N BOND FORMATION; INTRAMOLECULAR AMINOCARBONYLATION; CARBONYLATION REACTIONS; ASYMMETRIC-SYNTHESIS; SELECTIVE OXIDATION; ALPHA-AMINO; ALKYNES; FUNCTIONALIZATION;

D O I：

10.1021/jacs.5b00719

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel palladium-catalyzed intermolecular aminocarbonylation of alkenes has been developed in which the employment of hypervalent iodine reagent can accelerate the intermolecular aminopalladation, which thus provides the successful catalytic transformation. The current transformation presents one of the most convenient methods to generate beta-amino acid derivatives from simple alkenes.

引用

页码：2480 / 2483

页数：4

共 59 条

[31] Oxidative diamination of alkenes with ureas as nitrogen sources:: Mechanistic pathways in the presence of a high oxidation state palladium catalyst [J].

Muniz, Kilian ;

Hovelmann, Claas H. ;

Streuff, Jan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :763-773

[32] Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization [J].

Neufeldt, Sharon R. ;

Sanford, Melanie S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :936-946

[33]

Palomo C, 2001, SYNLETT, P1813

[34] Palladium-Catalyzed Selective Acyloxylation Using Sodium Perborate as Oxidant [J].

Pilarski, Lukasz T. ;

Janson, Par G. ;

Szabo, Kalman J. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1503-1506

[35] Catalytic Allylic C-H Acetoxylation and Benzoyloxylation via Suggested (η3-Allyl)palladium(IV) Intermediates [J].

Pilarski, Lukasz T. ;

Selander, Nicklas ;

Bose, Dietrich ;

Szabo, Kalman J. .

ORGANIC LETTERS, 2009, 11 (23) :5518-5521

[36] Bimetallic Redox Synergy in Oxidative Palladium Catalysis [J].

Powers, David C. ;

Ritter, Tobias .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :840-850

[37] Palladium-catalyzed oxidative Amination of alkenes: Improved catalyst reoxidation enables the use of alkene as the limiting reagent [J].

Rogers, Michelle M. ;

Kotov, Vasily ;

Chatwichien, Jaruwan ;

Stahl, Shannon S. .

ORGANIC LETTERS, 2007, 9 (21) :4331-4334

[38] The world of β- and γ-peptides comprised of homologated proteinogenic amino acids and other components [J].

Seebach, D ;

Beck, AK ;

Bierbaum, DJ .

CHEMISTRY & BIODIVERSITY, 2004, 1 (08) :1111-1239

[39]

Seebach D., 2009, Synthesis, V1

[40]

SEEBACH D, 1997, J CHEM SOC CHEM COMM, P2015, DOI DOI 10.1039/A704933A

← 1 2 3 4 5 6 →