Abstract
Optically active epoxides are known as versatile chiral building blocks in organic synthesis, and many efforts have been directed toward developing asymmetric epoxidation (AE) reaction of olefins. The first major breakthrough in AE using synthetic catalysts was realized by Katsuki and Sharpless in 1980, they achieved enantiomeric excesses (ee’s) greater than 90% in the titanium tartrate-based epoxidation of a variety of allylic alcohols. However, the substrates must bear specific functional groups to achieve the precoordination required for high enantioselectivity. In 1990 Jacobsen et al. and Katsuki et al. announced their independently developed systems for the catalytic AE of unfunctionalized olefins using chiral manganese (III) salen complexes. Since that time, the area of chiral manganese (III)- catalyzed AE has expanded greatly. In this review we will focus on the ligand development and the application of homogeneous chiral (salen) manganese (III)-promoted AE of olefins in recent years.
Keywords: Asymmetric epoxidation, Chiral, Manganese, Salen, homogeneous, Ligand, Olefin.
Current Organic Chemistry
Title:Asymmetric Epoxidation of Olefins with Homogeneous Chiral (Salen) Manganese (III) Complex
Volume: 17 Issue: 23
Author(s): Qian-Ping Shi, Zhi-Hao Shi, Nian-Guang Li, Yu-Ping Tang, Wei Li, Hao Tang, Wei-Zhang, Min-Zhe Shen and Jin-Ao Duan
Affiliation:
Keywords: Asymmetric epoxidation, Chiral, Manganese, Salen, homogeneous, Ligand, Olefin.
Abstract: Optically active epoxides are known as versatile chiral building blocks in organic synthesis, and many efforts have been directed toward developing asymmetric epoxidation (AE) reaction of olefins. The first major breakthrough in AE using synthetic catalysts was realized by Katsuki and Sharpless in 1980, they achieved enantiomeric excesses (ee’s) greater than 90% in the titanium tartrate-based epoxidation of a variety of allylic alcohols. However, the substrates must bear specific functional groups to achieve the precoordination required for high enantioselectivity. In 1990 Jacobsen et al. and Katsuki et al. announced their independently developed systems for the catalytic AE of unfunctionalized olefins using chiral manganese (III) salen complexes. Since that time, the area of chiral manganese (III)- catalyzed AE has expanded greatly. In this review we will focus on the ligand development and the application of homogeneous chiral (salen) manganese (III)-promoted AE of olefins in recent years.
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Cite this article as:
Shi Qian-Ping, Shi Zhi-Hao, Li Nian-Guang, Tang Yu-Ping, Li Wei, Tang Hao, Wei-Zhang , Shen Min-Zhe and Duan Jin-Ao, Asymmetric Epoxidation of Olefins with Homogeneous Chiral (Salen) Manganese (III) Complex, Current Organic Chemistry 2013; 17 (23) . https://dx.doi.org/10.2174/138527281723131218140657
DOI https://dx.doi.org/10.2174/138527281723131218140657 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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