5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine

被引：0

作者：

Bisaccia, Roberto ^{[1
,2
]}

Scafato, Patrizia ^{[1
]}

Casarini, Daniele ^{[1
]}

Superchi, Stefano ^{[1
]}

机构：

[1] Univ Basilicata, Dept Sci, Via Ateneo Lucano 10, I-85100 Potenza, Italy

[2] Flamma Grp, Via Bedeschi 22, I-20040 Bergamo, Italy

来源：

MOLBANK | 2023年 / 2023卷 / 01期

关键词：

dibenz[c; e]azepines; chirality sensing; atropisomerism; nitrones; 1,1'-BINAPHTHYLAZEPINE-BASED LIGANDS; ENANTIOSELECTIVE ADDITION; ASYMMETRIC ADDITION; TROPOS; HYDROXYLAMINES; CATALYSIS; OXIDATION; DESIGN; ROUTE; ZNET2;

D O I：

10.3390/M1554

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine has been synthesized as a possible pro-chiral (or tropos) unit for the construction of a chiral catalyst and as a molecular chirality sensor for the absolute configuration assignment by chiroptical spectroscopy. A straightforward synthetic strategy for the preparation of the title compound in high overall yield through sequential addition of the four methyl groups on benzylic positions has been described. A VT-NMR study was used to determine the rotational barrier of the aryl-aryl bond in this biphenylazepine, revealing its torsional flexibility at room temperature, which makes the biphenylazepine suitable as both a chirality probe and a tropos moiety in chiral ligands.

引用

页数：9

共 29 条

[1] DECOMPOSITION OF N-ARYLAZOAMINES [J].

AKHTAR, MH ;

OEHSCHLA.AC .

TETRAHEDRON, 1970, 26 (13) :3245-&

[2] Scorpio-Ligand: Synthesis of Biphenyl-Dihydroazepine Phosphoramidite Ligands for Asymmetric Hydrogenation [J].

Auras, Stefanie ;

Trapp, Oliver .

HELVETICA CHIMICA ACTA, 2021, 104 (11)

[3] Effect of polyfluorination on self-assembling and electronic properties of thioalkyl-porphyrazines [J].

Belviso, Sandra ;

Cammarota, Francesca ;

Rossano, Rocco ;

Lelj, Francesco .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2016, 20 (1-4) :223-233

[4]

Bottle S.E., 2007, WO Patent, Patent No. [2007124543A1, 2007124543]

[5] Inexpensive and environmentally friendly oxidation of hydroxylamines to nitrones with bleach [J].

Cicchi, S ;

Corsi, M ;

Goti, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7243-7245

[6] Indium-mediated reduction of hydroxylamines to amines [J].

Cicchi, S ;

Bonanni, M ;

Cardona, F ;

Revuelta, J ;

Goti, A .

ORGANIC LETTERS, 2003, 5 (10) :1773-1776

[7]

Gunther H., 2014, Nmr spectroscopy : basic principles, concepts and applications in chemistry

[8] Design of an axially chiral amino acid with a binaphthyl backbone as an organocatalyst for a direct asymmetric aldol reaction [J].

Kano, T ;

Takai, J ;

Tokuda, O ;

Maruoka, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3055-3057

[9] Efficient Organocatalytic Cross-Aldol Reaction between Aliphatic Aldehydes through Their Functional Differentiation [J].

Kano, Taichi ;

Sugimoto, Hisashi ;

Maruoka, Keiji .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18130-18133

[10] CHIRAL CATALYSIS OF ADDITIONS OF ALKYLLITHIUMS TO ALDEHYDES [J].

MAZALEYRAT, JP ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4585-4586

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