Catalytic Asymmetric Ring‐Opening Reaction of <i>meso</i>‐Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium‐Titanium‐Salen Complex

Sun, Jiangtao; Yang, Ming‐Hua; Fang, Yuan; Jia, Xuefeng; Yang, Xia; Pan, Yi; Zhu, Chengjian

doi:10.1002/adsc.200800767

Cited by 50 publications

(8 citation statements)

References 95 publications

(16 reference statements)

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“…For comparison, for analogous carbonyl structures with sulfide substituents, under these conditions, reduction of the carbonyl group occurred leading to the corresponding alcohols ( 18 [25], 22 ) as the only products in high yield. It means that attack on sulfur is not connected with the presence of a C–S bond but a sulfinyl substituent is required.…”

Section: Resultsmentioning

confidence: 99%

Phenylsilane as an effective desulfinylation reagent

Midura

Rzewnicka

Krysiak

2017

Beilstein J. Org. Chem.

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The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the α-position to the carboxylate group caused a desulfinylation product formation with full regio- and stereoselectivity, instead of a carbonyl group reduction. Investigations performed on different α-sulfinylcarbonyl compounds revealed that phenylsilane treatment constitutes a regiospecific method for the desulfinylation of a-sulfinylesters; for corresponding ketones the reaction course depends on the character of the carbonyl group.

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Section: Resultsmentioning

confidence: 99%

Phenylsilane as an effective desulfinylation reagent

Midura

Rzewnicka

Krysiak

2017

Beilstein J. Org. Chem.

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“…The reaction proceeds with good yield and high enantioselectivity enabling the synthesis of a enantioenriched β-hydroxy selenides (S,S)-54 (Scheme 26). [73,74] A scandiumbipyridine-catalysed enantioselective NROR of arylsubstituted meso-epoxides was also developed by Schneider et al Notably, a related sequential one-pot ring-opening-reduction protocol allowed the conversion of aryl meso-epoxides into enantioenrched 1,2- diaryl carbinols 57 via deselenylation of β-hydroxy selenide intermediates (R,R)-54 (Scheme 27). [75] Kreft et al reported the use of benzeneselenol in the ring-opening reaction of donor-acceptor cyclobutanes bearing two geminal ester groups as acceptors.…”

Section: Synthesis Of Selenium-containing Small Moleculesmentioning

confidence: 99%

Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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“…The authors proposed a strong synergistic effect between the two Lewis acids, with the hard Lewis acid titanium activating the epoxide and the softer gallium coordinating the arylselenol and directing the nucleophilic attack. The same method could also be extended to the ARO of meso-epoxides with thiols, resulting in high yields and moderate to high enantioselectivities (up to 92% ee) [85,86]. Scheme 25.…”

Section: With Thiols and Selenolsmentioning

confidence: 99%

Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

Lidskog

Wärnmark

2020

Catalysts

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The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems.

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Catalytic Asymmetric Ring‐Opening Reaction of meso‐Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium‐Titanium‐Salen Complex

Cited by 50 publications

References 95 publications

Phenylsilane as an effective desulfinylation reagent

Phenylsilane as an effective desulfinylation reagent

Synthesis and Applications of Organic Selenols

Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

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