Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C-H activation: unexpected inversion of the enantioselectivity induced by protic acids

被引：58

作者：

Nagamoto, Midori ^{[1
]}

Yamauchi, Daisuke ^{[1
]}

Nishimura, Takahiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 34期

关键词：

N-SULFONYL KETIMINES; BOND ACTIVATION; KETONES; EFFICIENT; FUNCTIONALIZATION; CYCLIZATION; 1,3-DIENES; IMINES; CARBOCYCLIZATION; HYDROGENATION;

D O I：

10.1039/c6cc01398h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic N-acyl ketimines with internal alkynes via C-H activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.

引用

页码：5876 / 5879

页数：4

共 58 条

[41] Tertiary Carbinamine Synthesis by Rhodium-Catalyzed [3+2] Annulation of N-Unsubstituted Aromatic Ketimines and Alkynes [J].

Sun, Zhong-Ming ;

Chen, Shuo-Ping ;

Zhao, Pinjing .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) :2619-2627

[42] New Approach for Complete Reversal of Enantioselectivity Using a Single Chiral Source [J].

Tanaka, Takanori ;

Hayashi, Masahiko .

SYNTHESIS-STUTTGART, 2008, (21) :3361-3376

[43] Hydroxyl-Directed Ruthenium-Catalyzed C-H Bond Functionalization: Versatile Access to Fluorescent Pyrans [J].

Thirunavukkarasu, Vedhagiri S. ;

Donati, Margherita ;

Ackermann, Lutz .

ORGANIC LETTERS, 2012, 14 (13) :3416-3419

[44] Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Allenes by the [3+2] Annulation of Aryl Ketimines [J].

Tran, Duc N. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10630-10634

[45] Enantioselective Rhodium(I)-Catalyzed [3+2] Annulations of Aromatic Ketimines Induced by Directed C?H Activations [J].

Tran, Duc N. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11098-11102

[46] syn-Selective Rhodium(I)-Catalyzed Allylations of Ketimines Proceeding through a Directed C-H Activation/Allene Addition Sequence [J].

Tran, Duc N. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) :8181-8184

[47] Sequential Catalytic Reactions for the Synthesis of Benzofulvenes Using an Iridium Complex with Dual Function [J].

Tsuchikama, Kyoji ;

Kasagawa, Mitsugu ;

Endo, Kohei ;

Shibata, Takanori .

SYNLETT, 2010, (01) :97-100

[48] Rhodium(III)-catalyzed Oxidative Coupling through C-H Bond Cleavage Directed by Phosphinoxy Groups [J].

Unoh, Yuto ;

Hashimoto, Yuto ;

Takeda, Daisuke ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2013, 15 (13) :3258-3261

[49] Mild Rhodium(III)-Catalyzed C-H Activation and Intermolecular Annulation with Allenes [J].

Wang, Honggen ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) :7318-7322

[50] Versatile Pyrrole Synthesis through Ruthenium(II)-Catalyzed Alkene C-H Bond Functionalization on Enamines [J].

Wang, Lianhui ;

Ackermann, Lutz .

ORGANIC LETTERS, 2013, 15 (01) :176-179

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