New optically pure sugar hydroperoxides. Synhtesis and use for enantioselective oxygen transfer

Hamann, Hans-Jürgen; Höft, Eugen; Mostowicz, Danuta; Mishnev, Anatoly; Urbańczyk‐Lipkowska, Zofia; Chmielewski, Marek

doi:10.1016/s0040-4020(96)00962-3

Cited by 67 publications

(33 citation statements)

References 10 publications

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“…1 Recently we described the asymmetric epoxidation of allylic alcohols and the oxidation of sulfides to sulfoxides with optically active sugar hydroperoxides. 2,3,4 Enantioselectivities up to 50% e. e. were observed. Because the Jacobsen method 1 using Mn-salen-complexes works highly efficient only for cis-substituted olefins the epoxidation of unfunctionalized olefins is still a great challenge in asymmetric oxidation.…”

Section: Introductionmentioning

confidence: 94%

Enantioselective epoxidation of 1-hexene with sugar derived hydroperoxides

Hamann¹,

Chmielewski²,

Mostowich³

et al. 2006

Arkivoc

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Section: Introductionmentioning

confidence: 94%

Enantioselective epoxidation of 1-hexene with sugar derived hydroperoxides

Hamann¹,

Chmielewski²,

Mostowich³

et al. 2006

Arkivoc

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“…[53] The authors demonstrated that the hydroperoxides 214 could easily be transformed into the α-methylene δ-lactones 211a or 211b in the presence of an acetic anhydride/pyridine mixture. The starting hydroperoxides 214 were obtained by oxidation of 212 or 213 with H 2 O 2 / MoO 3 .…”

Section: Application Of Sugar Derivatives In the Synthesis Of Polyhydmentioning

confidence: 99%

Recent Advances in the Synthesis of α‐Alkylidene‐Substituted δ‐Lactones, γ‐Lactams and δ‐Lactams

2011

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α-Alkylidene-substituted δ-lactones and corresponding γ-and δ-lactams constitute important classes of natural compounds that display diverse biological activities. This review gives a brief description of the occurrence and biological activities of the title compounds and then summarizes the methods available for their preparation. Attention is given mainly to the synthetic approaches developed during the last decade, including those from our own research group. The latest developments in the synthesis of nonracemic α-alkylidene-substituted δ-lactones, γ-lactams and δ-lactams are also discussed.

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“…3 In the latter strategy, asymmetric oxygen transfer reagents, such as chiral hydroperoxides can be applied. [4][5][6] As an alternative, chiral catalysts or chiral reagents in the presence of non-chiral oxidizing reagents (t-butyl hydroperoxide, cumene hydroperoxide, oxone or hydrogen peroxide) have been used. 7 Selective oxidations of sulphides 1 to sulphoxides 2 is challenging due to the sensibility to overoxidation to achiral sulphones 3.…”

Section: Introductionmentioning

confidence: 99%

Isoquinoline- and piperazinedione-derived α-acylamino peroxide moieties in asymmetric oxidation of sulphides and epoxidation of naphthoquinones

Blumenthal

Liebscher²

2009

Arkivoc

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The application of chiral α-acylamino hydroperoxide moieties in asymmetric sulphoxidation and epoxidations was pursued. In order to synthesize new isoquinoline-derived α-acylamino hydroperoxides isoquinolines were treated with (R)-menthyl chloroformate and hydrogen peroxide. Instead of the expected hydroperoxides novel bis(2-menthyloxycarbonyl-1,2-dihydroisoquinolin-1-yl) peroxides were obtained as 1:1 epimeric mixtures by a subsequent reaction. 1:1 mixtures of t-butyl (2-menthyloxycarbonyl-1,2-dihydroisoquinolin-1-yl) peroxides were formed from t-butyl hydroperoxide, isoquinoline and (R)-menthyl chloroformate. For eventual in situ preparation of chiral (R)-menthyloxycarbonyl-1,2-dihydroisoquinolin-1-yl) hydroperoxides and their application in stereoselective O-transfer reactions, isoquinolines were combined with (R)-menthyl chloroformate, hydrogen peroxide and metal alkoxides. These mixtures allowed a stereoselective synthesis of aryl methyl sulphoxides from corresponding sulphides. The stereoselectivity results from a kinetic resolution of racemic sulphoxides formed in the first step wherein the (S)-enantiomer was faster oxidized to the corresponding sulphone. As another type of chiral α-acylamino hydroperoxide moiety piperazinedione hydroperoxide was applied in the transformation of aryl methyl sulphides into sulphoxides. Low enantioselectivities were achieved. The same reagent allowed a high yielding epoxidation of naphthoquinones, but again in modest stereoselectivities.

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New optically pure sugar hydroperoxides. Synhtesis and use for enantioselective oxygen transfer

Cited by 67 publications

References 10 publications

Enantioselective epoxidation of 1-hexene with sugar derived hydroperoxides

Enantioselective epoxidation of 1-hexene with sugar derived hydroperoxides

Recent Advances in the Synthesis of α‐Alkylidene‐Substituted δ‐Lactones, γ‐Lactams and δ‐Lactams

Isoquinoline- and piperazinedione-derived α-acylamino peroxide moieties in asymmetric oxidation of sulphides and epoxidation of naphthoquinones

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