Synthesis of optically active tellurium-containing binaphthyls and their use in the asymmetric 1,4-addition reaction of α,β-unsaturated ketones

Irie, Masaki; Doi, Yoshiko; Ohsuka, Masahiro; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio

doi:10.1016/s0957-4166(00)80056-7

Cited by 8 publications

(3 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The acetal 2 (3.3g, 9.9 mmol) was hydrolyzed with HCl (6 N, 7 mL) as reported 9c and purified by flash column chromatography over silica (60-120 mesh, petroleum ether-ethyl acetate 95:5) to give 4 as a reddish yellow liquid (2.6 g, 91%). (5). Recrystallization of the light orange solid obtained during the preparation of 2 from chloroform-hexane (1:1) afforded pure 5 as the major product: yield 1.5 g, 24%; mp 120 °C).…”

Section: Synthesis Of O-(butyldibromotelluro)benzaldehydementioning

confidence: 99%

“…Earlier we reported the attempted synthesis of some “hybrid” chiral tellurium ligands and structural characterization of one of the derivatives . Recently, synthesis of optically active tellurium-containing binaphthyls, and bis[2-(1-(dimethylamino)ethyl)ferrocenyl] dichalcogenides and their applications in chiral induction have been investigated. Very recently, the first examples of chirality transfer in allylic telluroxides and diastereoselective imination of a chiral cinnamyl ferrocenyl telluride 8 have been reported.…”

Section: Introductionmentioning

confidence: 99%

“…Earlier we reported the attempted synthesis of some "hybrid" chiral tellurium ligands and structural characterization of one of the derivatives. 4 Recently, synthesis of optically active tellurium-containing binaphthyls, 5 and bis-[2-(1-(dimethylamino)ethyl)ferrocenyl] dichalcogenides 6 and their applications in chiral induction have been investigated. Very recently, the first examples of chirality transfer in allylic telluroxides 7 and diastereoselective imination of a chiral cinnamyl ferrocenyl telluride 8 applications of chiral tellurium and selenium ligands in asymmetric catalysis, we contemplated the synthesis of conformationally more rigid polydentate chiral tellurium azomethines, incorporating mixed donor atoms, which may provide a high degree of stereocontrol in organic reactions.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Reactivity of Chiral Tellurium Azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-Hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl]tellurium(IV) Bromide

et al. 1997

View full text Add to dashboard Cite

A range of novel chiral tellurium compounds having an azomethine functional group in the position ortho to tellurium has been synthesized by the reaction of the tellurium-containing aldehydes bis(o-formylphenyl) telluride (1) and o-(butyltelluro)benzaldehyde (4) with chiral amines (R)-(+)-(1-pheylethylamine) and (1R,2S)-(−)-norephedrine, respectively. The precursor aldehydes were prepared by using a reported procedure with slight but advantageous modifications. During the preparation of o-(butyltelluro)benzaldehyde, interesting side products, namely bis(o-formylphenyl) ditelluride ethylene acetal 5, bis(o-formylphenyl) tritelluride (6), and bis(o-formylphenyl) ditelluride (7) were isolated in moderate yields. The ditelluride 7 has been characterized by single-crystal X-ray diffraction studies. The liquid Schiff bases 10 and 11 were further characterized by derivatizing with liquid bromine. The title compound was obtained in excellent yield by reacting the Schiff base 11 with elemental bromine. Detailed NMR studies indicated the presence of a rigid environment for the hydroxyl group. Single-crystal X-ray determinations of the crystals obtained from the different batches indicated the presence of the two pseudopolymorphic forms 13a and 13b, respectively. In the case of 13a there is one molecule of CH3CN as solvent of crystallization, whereas in 13b half a molecule of CH3CN per molecule of the title compound lies along the 2-fold axis. In 13a the hydroxyl hydrogen is hydrogen-bonded to the nitrogen of the solvent molecule, whereas in 13b it is hydrogen-bonded to the bromine of the neighboring molecule.

show abstract

Section: Synthesis Of O-(butyldibromotelluro)benzaldehydementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Reactivity of Chiral Tellurium Azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-Hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl]tellurium(IV) Bromide

et al. 1997

View full text Add to dashboard Cite

show abstract

Synthesis of Organotellurium Compounds

Zade

Singh

2012

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

This chapter highlights recent progress in the synthetic approaches to organotellurium chemistry and syntheses of novel compounds since 1987. Each section deals with a class of organotellurium compounds having tellurium in the particular functional group such as ditellurides, tellurides, tellurols, tellurones, tellurenyl halides and related derivatives, telluronium salts, telluroxanes, etc. Each section has been further subdivided according to the reaction types used for the preparation of the compounds. The chapter is based on over 150 original references.

show abstract

ChemInform Abstract: Synthesis of Optically Active Tellurium‐Containing Binaphthyls and Their Use in the Asymmetric 1,4‐Addition Reaction of α,β‐ Unsaturated Ketones.

et al. 1994

View full text Add to dashboard Cite

show abstract

Synthesis of optically active tellurium-containing binaphthyls and their use in the asymmetric 1,4-addition reaction of α,β-unsaturated ketones

Cited by 8 publications

References 12 publications

Synthesis and Reactivity of Chiral Tellurium Azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-Hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl]tellurium(IV) Bromide

Synthesis and Reactivity of Chiral Tellurium Azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-Hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl]tellurium(IV) Bromide

Synthesis of Organotellurium Compounds

ChemInform Abstract: Synthesis of Optically Active Tellurium‐Containing Binaphthyls and Their Use in the Asymmetric 1,4‐Addition Reaction of α,β‐ Unsaturated Ketones.

Contact Info

Product

Resources

About