Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

被引：41

作者：

Tanaka, Takafumi ^{[1
]}

Tanaka, Tsukushi ^{[1
]}

Tsuji, Taro ^{[1
]}

Yazaki, Ryo ^{[1
]}

Ohshima, Takashi ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

关键词：

BOND-DISSOCIATION ENERGIES; C-H BONDS; OXIDATION; METAL; DIMERIZATION; ACTIVATION; ACIDITIES; KETONE; ROUTE; ACYLPYRAZOLES;

D O I：

10.1021/acs.orglett.8b01313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural alpha,alpha-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

引用

页码：3541 / 3544

页数：4

共 55 条

[31] Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides [J].

Kaiser, Daniel ;

Teskey, Christopher J. ;

Adler, Pauline ;

Maulide, Nuno .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) :16040-16043

[32] PHOTO-OXIDATION OF SOME MESOIONIC AND RELATED SYSTEMS [J].

KATO, H ;

TANI, K ;

KURUMISAWA, H ;

TAMURA, Y .

CHEMISTRY LETTERS, 1980, (06) :717-720

[33] Guanidinium Hydroiodide/Cumene Hydroperoxide-Mediated Intermolecular Oxidative Coupling Reaction of β-Ketoamides with Oxindoles [J].

Kato, Takanari ;

Yasui, Koji ;

Odagi, Minami ;

Nagasawa, Kazuo .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (16) :2881-2889

[34]

Kozlowski M. C, 2017, ACCOUNTS CHEM RES, V50, P638

[35] Iron-Catalyzed Oxidative C-H/C-H Cross-Coupling: An Efficient Route to α-Quaternary α-Amino Acid Derivatives [J].

Li, Kaizhi ;

Tan, Guangying ;

Huang, Jingsheng ;

Song, Feijie ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) :12942-12945

[36] Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions [J].

Liu, Chao ;

Zhang, Hua ;

Shi, Wei ;

Lei, Aiwen .

CHEMICAL REVIEWS, 2011, 111 (03) :1780-1824

[37] GENERATION AND FATE OF FREE-RADICALS OF DELTA-2-OXAZOLIN-5-ONES [J].

MARQUEZ, A ;

CHUAQUI, CA ;

RODRIGUEZ, H ;

ZAGAL, L .

TETRAHEDRON, 1985, 41 (12) :2341-2346

[38] Potential of Metal-Catalyzed C-C Single Bond Cleavage for Organic Synthesis [J].

Murakami, Masahiro ;

Ishida, Naoki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (42) :13759-13769

[39] GENERATION OF CATION RADICALS FROM ENAMINES AND THEIR REACTIONS WITH OLEFINS [J].

NARASAKA, K ;

OKAUCHI, T ;

TANAKA, K ;

MURAKAMI, M .

CHEMISTRY LETTERS, 1992, (10) :2099-2102

[40]

OHTA S, 1987, CHEM PHARM BULL, V35, P1058

← 1 2 3 4 5 6 →