2004
DOI: 10.1021/ar030063x
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Organocatalytic Asymmetric Epoxidation of Olefins by Chiral Ketones

Abstract: Chiral ketones have been shown to be effective organocatalysts for asymmetric epoxidation of olefins with broad substrate scope. High enantioselectivity has been obtained for a wide variety of trans and trisubstituted olefins, as well as a number of cis olefins, with encouragingly high ee's for some terminal olefins. The stereochemical outcome of the reaction can be rationalized by a spiro transition state model.

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Cited by 438 publications
(175 citation statements)
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“…[4,5] Such a system has recently been reported by Beller and colleagues for enantioselective epoxidations based on iron catalysts and hydrogen peroxide as oxidant. [6] In addition, chiral ketones instead of transition metals are increasingly recognized as valuable organocatalysts for asymmetric epoxidations, [7] as well as the use of molecular oxygen instead of hazardous, waste producing oxidants. [8] Although many of these future-oriented methodologies show already promising enantioselectivities, low catalyst efficiencies and low productivities often restrict their practical value.…”
Section: Introductionmentioning
confidence: 99%
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“…[4,5] Such a system has recently been reported by Beller and colleagues for enantioselective epoxidations based on iron catalysts and hydrogen peroxide as oxidant. [6] In addition, chiral ketones instead of transition metals are increasingly recognized as valuable organocatalysts for asymmetric epoxidations, [7] as well as the use of molecular oxygen instead of hazardous, waste producing oxidants. [8] Although many of these future-oriented methodologies show already promising enantioselectivities, low catalyst efficiencies and low productivities often restrict their practical value.…”
Section: Introductionmentioning
confidence: 99%
“…[8] Although many of these future-oriented methodologies show already promising enantioselectivities, low catalyst efficiencies and low productivities often restrict their practical value. [5,7] A potential solution for these challenges is the utilization of enzymatic epoxidation catalysts, that is, monooxygenases. Monooxygenases frequently exhibit high conversion rates at excellent enantioselectivities, are active at ambient reaction conditions, use molecular oxygen as oxidant, and are produced from natural, renewable raw materials.…”
Section: Introductionmentioning
confidence: 99%
“…The stereochemical outcome of the reaction has been rationalized on the basis of a spiro transition state. 13 Very mild homogeneous conditions have been elaborated for the in situ generation of dioxiranes from ketones using a buffered Oxone solution. Page and co-workers have reported a noteworthy advance in asymmetric epoxidations of unfunctionalized olefins using chiral iminium salts, such as 26.…”
Section: Epoxides Preparation Of Epoxidesmentioning
confidence: 99%
“…The allyl alcohol 6 would be derived from regioselective epoxide ring opening reaction of epoxide 7, which in turn would be obtained by the chemoand enantioselective epoxidation of 8 by the Shi asymmetric epoxidation protocol. [15][16][17] The bicyclic compound 8 can be easily prepared by the procedure in our previous report. 12) This synthetic project was started from the introduction of an asymmetric carbon to bicyclic lactone by Shi asymmetric epoxidation as shown in Chart 2.…”
mentioning
confidence: 99%