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Diastereoselective Epoxidation Of Allylically Substituted Alkenes Using Metalloporphyrin Catalysts

Summary

Diastereoselective Epoxidation Of Allylically Substituted Alkenes Using Metalloporphyrins As Catalyst Provides High Trans-Selectivities (I.E., Trans-:Cis-Epoxide Ratio). A Diversity Of Cycloalkenes Bearing Different Allylic Substituents Are Shown To Be Efficiently Epoxidized To Afford The Corresponding Trans-Epoxides With Excellent Trans-Selectivities (Up To >98%) And Good Yields (Up To 99%). Acyclic Allylic Alkenes Bearing Different Allylic Substituents Are Efficiently Epoxidized To Afford The Corresponding Erythro-Epoxides With Good Erythro-Selectivities. The Metalloporphyrin-Catalyzed Reactions Exhibit Up To 20 Times Higher Trans-Selectivities Than The Conventional Method Using M-Chloroperoxybenzoic Acid As Oxidant.

Supplementary Information

Patent Number: US7482478B2
Application Number: US200580436A
Inventor: Che, Chi-Ming | Wong, Man-Kin
Priority Date: 18 Mar 2004
Priority Number: US7482478B2
Application Date: 16 Mar 2005
Publication Date: 27 Jan 2009
IPC Current: C07D030112 | B01J003118 | B01J003126 | B01J003128 | B01J003132 | C07D030106 | C07D030114 | C07D030119 | C07D040506 | C07D048722
US Class: 549531 | 549524
Assignee Applicant: The University of Hong Kong
Title: Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrin catalysts
Usefulness: Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrin catalysts
Summary: Used in the preparation of trans-/erythro-epoxide (claimed), which is useful in the synthesis of natural products and chiral drugs.
Novelty: Preparation of a trans-/erythro-epoxide, which is useful in the synthesis of natural products and chiral drugs, comprises catalyzing the reaction of an oxidant with the alkene compound in the presence of metalloporphyrin catalyst

Industry

Chemical/Material

Sub Category

Chemical/Material Application

Application No.

US200580436A

Country/Region

Hong Kong