[reaction: see text] An efficient and straightforward method for the preparation of highly enantiomerically enriched C2-symmetrical vicinal diamines by the reductive homocoupling of aromatic N-tert-butanesulfinyl imines in the presence of SmI2 and HMPA was developed. It gives access to a variety of enantiopure C2-symmetrical 1,2-diamines in a very mild and practical way.
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http://dx.doi.org/10.1021/ol0479803 | DOI Listing |
Angew Chem Int Ed Engl
May 2016
Dipartimento di Chimica, Sapienza University of Roma, P. le Aldo Moro 5, 00185, Roma (I, Italy.
Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones to afford non-C2 -symmetrical, axially chiral biaryl products, which are promising compounds as chiral ligands and organocatalysts. The rotational barrier required to have two distinct atropisomers has been evaluated in the products generated from the addition of naphthols to various quinones by means of DFT calculations and HPLC. The use of halogenated quinones as reagents was necessary to have configurationally stable enantiomeric products which can be obtained in good yield and stereoselectivity.
View Article and Find Full Text PDFBioorg Med Chem Lett
August 2013
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, China.
Four novel iridium(III) complexes with enantiopure C2-symmetrical vicinal diamine ligands were designed, synthesized, and characterized by FT-IR, NMR, and MS. The cytotoxicities of all of the complexes against the human solid tumor cell lines A2780, A549, KB, and MDA-MB-231 were evaluated. Both R,R-configured complexes (R,R)-5a and (R,R)-5b exhibited more potent or similar activity compared with oxaliplatin, whereas their corresponding (S,S)-isomers (S,S)-5a and (S,S)-5b were found to be mostly inactive.
View Article and Find Full Text PDFJ Org Chem
July 2011
Department of Chemistry, National Taiwan University, Taipei, Taiwan.
The design, synthesis, conformational analysis, and variable-temperature NMR studies of pentiptycene-based molecular gears Pp(2)X, where Pp is the unlabeled (in 1H) or methoxy groups-labeled (in 1OM) pentiptycene rotor and X is the phenylene stator containing ortho-bridged ethynylene axles, are reported. The approach of using shape-persistent rotors of four teeth but C(2) symmetry for constructing four-toothed molecular gears is unprecedented. In addition, the first example of enantioresolution of chiral pentiptycene scaffolds is demonstrated.
View Article and Find Full Text PDFJ Org Chem
April 2007
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16 43007 Tarragona, Spain.
Suzuki arylation of enantiopure (4-bromophenyl)- or (3,5-dibromophenyl)glycidyl ethers has been achieved in toluene under Buchwald conditions [ArB(OH)2 (1.1 equiv), Cs2CO3 (2 equiv), Pd2(dba)3.C6H6 (1 mol %), S-Phos (4 mol %), toluene, 100 degrees C] allowing for the formation of modular arylglycidyl ethers not directly available in enantiopure form by epoxidation routes.
View Article and Find Full Text PDFOrg Lett
December 2004
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
[reaction: see text] An efficient and straightforward method for the preparation of highly enantiomerically enriched C2-symmetrical vicinal diamines by the reductive homocoupling of aromatic N-tert-butanesulfinyl imines in the presence of SmI2 and HMPA was developed. It gives access to a variety of enantiopure C2-symmetrical 1,2-diamines in a very mild and practical way.
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