A Catalytic Cycle for the Asymmetric Synthesis of Epoxides Using Sulfur Ylides

Zanardi, Jacques; Leriverend, Catherine; Aubert, Dimitri; Julienne, Karine; Metzner, Patrick

doi:10.1021/jo015588m

Cited by 116 publications

(55 citation statements)

References 23 publications

(18 reference statements)

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“…15,19 We had devised a very simple procedure. All reagents are mixed at the start: chiral sulfide, benzyl bromide, sodium iodide, aldehyde, sodium hydroxide and a 9:1 tert-butanol/water mixture as solvent.…”

Section: Evaluation Of Planar Chiral Sulfides As Source Of Ylides Formentioning

confidence: 99%

“…We are interested in the synthesis of oxiranes by the Johnson-Corey reaction of sulfur ylides with aldehydes. [10][11][12] We have recently reported [13][14][15][16][17] an aliphatic C 2 symmetric sulfide, 2,5-dimethylthiolane, as a chiral auxiliary used in a catalytic amount for this reaction, which could be performed easily with yields and enantiomeric excesses around 90% (Scheme 1). …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes

Minière¹,

Reboul

Metzner³

2005

Arkivoc

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New ferrocenyl sulfides, exhibiting planar chirality, have been prepared. They incorporate various heteroatom groups, and in some cases central chirality (sulfur or carbon). They were evaluated as catalysts for the asymmetric epoxidation of aldehydes via sulfonium ylides. A onepot reaction has been achieved, involving addition of benzaldehyde, benzyl bromide, 20% molar equivalent of the ferrocenyl sulfide, sodium iodide in a mixture of tert-butanol and water. Good yields of stilbene oxide were obtained, with enantiomeric excesses up to 53%.

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Section: Evaluation Of Planar Chiral Sulfides As Source Of Ylides Formentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes

Minière¹,

Reboul

Metzner³

2005

Arkivoc

Self Cite

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“…(486) is a convenient test system for such procedures (Scheme 2.73). The 2,5-dimethylthiolane (477) was used in a one-pot stoichiometric variant of this reaction (Table 2.17, entry 1), providing the (S,S)-epoxide in excellent yield and good enantioselectivity [518]; even higher optical purity was obtained simply by using the diethyl analog 478 [519].…”

Section: Epoxidation Of Carbonyl Compoundsmentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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“…Furthermore epoxides are useful and important synthetic precursors and have found divers applications in organic synthesis [14,15]. There are many reports on the synthesis of epoxides possessing various heterocyclic moieties [16][17][18]. However synthesis and reactions of pyrone sulfonium salts and corresponding ylides with arene carbaldehydes have not been reported as yet.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides

Shahrisa

Saraei

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Hexaminium salts of 4-pyrones 3a, b were synthesized by treatment of 2-(4-bromomethylphenyl)-6-methyl-4H-pyran-4-one 2a and 2-(4-bromomethylphenyl)-6-phenyl-4H-pyran-4-one 2b with hexamethylenetetramine in chloroform in 71 and 84% yields respectively. Hydrolysis of 3a and 3b in EtOH:H 2 O produced the corresponding aldehydes 4a and 4b in 43 and 58% yields respectively. The reaction of bromopyrones 2b and 2c with dimethylsulfide in MeOH: CH 2 Cl 2 afforded the corresponding sulfonium salts 5b and 5c in 66 and 65% yields respectively. Treatment of 5b and 5c with arene carbaldehydes such as (Ar ¼ p-ClC 6 H 4 , o-ClC 6 H 4 , p-NO 2 C 6 H 4 , o-NO 2 C 6 H 4 , p-FC 6 H 4 , 2-naphthyl, p-MeOC 6 H 4, C 6 H 5 CH¼ ¼CH, p-MeC 6 H 4 , C 6 H 5 and 4-(4-oxo-6-phenyl-4H-pyran-2-yl)-benzaldehyde 4b) in the presence of sodium hydroxide in CH 3 CN:H 2 O afforded eleven trans-epoxides in 61-93% yields.

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A Catalytic Cycle for the Asymmetric Synthesis of Epoxides Using Sulfur Ylides

Cited by 116 publications

References 23 publications

Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes

Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes

Three‐Membered Heterocycles. Structure and Reactivity

Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides

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