Catalytic imine-imine cross-coupling reactions

被引：49

作者：

Matsumoto, Masatoshi ^{[1
]}

Harada, Masashi ^{[1
]}

Yamashita, Yasuhiro ^{[1
]}

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 86期

基金：

日本学术振兴会;

关键词：

POTENTIAL CHIRAL SUPERBASES; LOW-VALENT TITANIUM; CHLORIDE-INDUCED CYCLIZATION; IN-SITU GENERATION; MODIFIED GUANIDINES; AROMATIC-ALDEHYDES; VICINAL DIAMINES; GLYCINE ESTERS; DERIVATIVES; ALDIMINES;

D O I：

10.1039/c4cc06156j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report here efficient catalytic imine-imine cross-coupling reactions based on an umpolung strategy; an imine bearing a 9-fluorenyl moiety on its nitrogen atom, which acted as a nucleophile, reacted with another imine to afford an imine-imine cross-coupling adduct in high yield. Furthermore, a chiral guanidine acted as a chiral catalyst for these coupling reactions, and optically active 1,2-diamines were obtained in high yields with high enantioselectivities.

引用

页码：13041 / 13044

页数：4

共 38 条

[1] PREPARATION OF 1,2-DIARYLETHYLENEDIAMINES BY AMINATIVE REDUCTIVE COUPLING OF AROMATIC-ALDEHYDES WITH LOW-VALENT TITANIUM REAGENTS [J].

BETSCHART, C ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1987, 70 (08) :2215-2231

[2] ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES [J].

BUCHWALD, SL ;

WATSON, BT ;

WANNAMAKER, MW ;

DEWAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4486-4494

[3] Catalytic Carbon-Carbon Bond-Forming Reactions of Aminoalkane Derivatives with Imines [J].

Chen, Yi-Jing ;

Seki, Kazutaka ;

Yamashita, Yasuhiro ;

Kobayashi, Shu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3244-+

[4] Biotin: A timeless challenge for total synthesis [J].

DeClercq, PJ .

CHEMICAL REVIEWS, 1997, 97 (06) :1755-1792

[5] New developments in the chemistry of low-valent titanium [J].

Furstner, A ;

Bogdanovic, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21) :2442-2469

[6]

Gao Y, 1997, SYNLETT, P1353

[7] Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams [J].

Guizzetti, Stefania ;

Benaglia, Maurizio ;

Bonsignore, Martina ;

Raimondi, Laura .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) :739-743

[8] Chiral Lanthanum(III)-Binaphthyldisulfonate Complexes for Catalytic Enantioselective Strecker Reaction [J].

Hatano, Manabu ;

Hattori, Yasushi ;

Furuya, Yoshiro ;

Ishihara, Kazuaki .

ORGANIC LETTERS, 2009, 11 (11) :2321-2324

[9] SAMARIUM DIIODIDE-PROMOTED REDUCTIVE COUPLING OF IMINES [J].

IMAMOTO, T ;

NISHIMURA, S .

CHEMISTRY LETTERS, 1990, (07) :1141-1142

[10] Modified guanidines as potential chiral superbases. 3. Preparation of 1,4,6-triazabicyclooctene systems and l,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent [J].

Isobe, T ;

Fukuda, K ;

Yamaguchi, K ;

Seki, H ;

Tokunaga, T ;

Ishikawa, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7779-7785

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