Chiral Vanadium-Based Catalysts for Asymmetric Epoxidation of Allylic Alcohols

Murase, Naruhiko; Hoshino, Yujiro; Oishi, M.; Yamamoto, Hisashi

doi:10.1021/jo9821933

Cited by 92 publications

(38 citation statements)

References 13 publications

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“…It has been demonstrated that the VO(OiPr) 3 complex is the most efficient catalyst for the epoxidation reaction and that the nature of the solvent can affect the level of enantioselectivity. [4][5][6][7][8][9][10][11] Scheme 1. Vanadium-catalyzed epoxidation of allylic alcohols.…”

Section: Resultsmentioning

confidence: 99%

Vanadium‐Catalyzed Asymmetric Epoxidation of Allylic Alcohols Mediated by (+)‐Norcamphor‐Derived Hydroperoxide

2005

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A protocol for the asymmetric epoxidation of allylic alcohols has been established that employs VO(acac)2 as catalyst, the commercial achiral hydroxamic acid, N‐hydroxy‐N‐phenylbenzamide, and optically pure (+)‐norcamphor‐derived hydroperoxide as oxygen atom donor and chiral source. Variation of the reaction parameters has a significant effect on the level of asymmetric induction. Under optimized conditions, the epoxy alcohols have been isolated in good yields with up to 67 % ee and complete control of the diastereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

Vanadium‐Catalyzed Asymmetric Epoxidation of Allylic Alcohols Mediated by (+)‐Norcamphor‐Derived Hydroperoxide

2005

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“…For example, Hussain and Walsh [449] have developed a Sharplessinspired tandem alkylation/epoxidation of prochiral enones to provide chiral nonracemic hydroxyepoxides. Yamamoto and coworkers [450] …”

Section: Oxiranes J73mentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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“…While the titanium-catalyzed epoxidation reaction was flourishing, the pioneer version of the reaction remained undeveloped and it was not until 1999 that new discoveries in vanadium-catalyzed AE were revealed [33]. In the epoxidation of various allylic alcohols, the hydroxamic acid of structure 4 ( Figure 6.6) was presented as the best ligand for vanadium, allowing enantiomeric excesses of up to 94 % [33,34].…”

Section: Vanadium-catalyzed Epoxidationsmentioning

confidence: 99%

“…In the epoxidation of various allylic alcohols, the hydroxamic acid of structure 4 ( Figure 6.6) was presented as the best ligand for vanadium, allowing enantiomeric excesses of up to 94 % [33,34].…”

Section: Vanadium-catalyzed Epoxidationsmentioning

confidence: 99%