Catalytic imine-imine cross-coupling reactions

被引：48

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
BETSCHART, C
SEEBACH, D
[J]. 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
BUCHWALD, SL
WATSON, BT
WANNAMAKER, MW
DEWAN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4486 - 4494
[3] Catalytic Carbon-Carbon Bond-Forming Reactions of Aminoalkane Derivatives with Imines
Chen, Yi-Jing
Seki, Kazutaka
Yamashita, Yasuhiro
Kobayashi, Shu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3244 - +
[4] Biotin: A timeless challenge for total synthesis
DeClercq, PJ
[J]. CHEMICAL REVIEWS, 1997, 97 (06) : 1755 - 1792
[5] New developments in the chemistry of low-valent titanium
Furstner, A
Bogdanovic, B
[J]. 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
Guizzetti, Stefania
Benaglia, Maurizio
Bonsignore, Martina
Raimondi, Laura
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) : 739 - 743
[8] Chiral Lanthanum(III)-Binaphthyldisulfonate Complexes for Catalytic Enantioselective Strecker Reaction
Hatano, Manabu
Hattori, Yasushi
Furuya, Yoshiro
Ishihara, Kazuaki
[J]. ORGANIC LETTERS, 2009, 11 (11) : 2321 - 2324
[9] SAMARIUM DIIODIDE-PROMOTED REDUCTIVE COUPLING OF IMINES
IMAMOTO, T
NISHIMURA, S
[J]. 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
Isobe, T
Fukuda, K
Yamaguchi, K
Seki, H
Tokunaga, T
Ishikawa, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) : 7779 - 7785

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